Category: 928-92-7

Synthetic Route of 928-92-7 ,Some common heterocyclic compound, 928-92-7, molecular formula is C6H12O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a stirred solution of oxalyl chloride (5.23 mL 60 mmol) in 50 mL dry CH2Cl2 at -78°C under Argon, dimethyl sulfoxide ( 8.51 mL, 120 mmol) in 5 mL dry CH2Cl2 was added slowly. The reaction mixture was allowed to stirr for next 15 min. 4-Hexen-1-ol (4.7 mL, 40 mmol) in 10 mLCH2Cl2 was added dropwise to the reaction mixture and stirring was continued for next 45 min at -78°C. Further, Et3N (33.38 mL, 240 mmol) was added dropwise at 0°C and the reaction mixture was allowed to stirr for next 1 h (Foul smell of dimethyl sulfide). This was further treated with benzyl(triphenylphosphoranylidene)acetate (19.7 g, 48 mmol) in 70 mL dry CH2Cl2 and wasallowed to stirr for next 12 h at room temperature. Then, the reaction mixture was quenched withwater and extracted with excess CH2Cl2 and brine. The organic phase was separated, dried over MgSO4 and evaporated under reduced pressure. The crude brownish oil was subjected to column chromatography. The product (8) was separated as light yellow oil (95:5, E:Z) at gradient(hexane/ethyl acetate, 95:5) (7.73 g, 84percent).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 928-92-7, 4-Hexen-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Holla, Harish; Labaied, Mehdi; Pham, Ngoc; Jenkins, Ian D.; Stuart, Kenneth; Quinn, Ronald J.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 16; (2011); p. 4793 – 4797;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.928-92-7, name is 4-Hexen-1-ol, molecular formula is C6H12O, molecular weight is 100.16, as common compound, the synthetic route is as follows.Formula: C6H12O

trans-4-hexene-1-ol(16, 40.0 g, 0.4 mol) and Et3N (48.5 g, 0.48 mol) weredissolved in toluene 400 mL. MsCl (50.3 g, 0.44 mol) was then dropped into this solution,which was cooled with ice, keeping the reaction temperature at 25C or less. After agitatingfor 1 hr, brine 200 mL was added. The organic layer was washed twice using 5 wt%NaHCO3 solution 500 mL and water 500 mL. After drying with MgSO4, the toluene wasconcentrated. As a result, 4-hexene-1-mesylate (17, 69.5 g, 0.39 mol, yield: 97.5%) wasobtained as a colorless, oily substance.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,928-92-7, 4-Hexen-1-ol, and friends who are interested can also refer to it.

Reference:
Article; Gotoh, Yasuyuki; Ushioda, Makoto; Molecular Crystals and Liquid Crystals; vol. 593; 1; (2014); p. 61 – 77;,
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Synthetic Route of 928-92-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 928-92-7 as follows.

Example 5; Methyl 5-methyl-3,4-dihydro-2H-pyrano [2,3-c] pyridine-6-carboxylate(a) (is)-Methyl 2-((2-(hex-4-en-l-yloxy)-2-oxoethyl)amino)-2-oxoacetateTo a vessel maintained at 40 ¡ãC was charged CDI (2.75 g, 0.95 eq) and TBME (9 mL). To this mixture was added with stirring a solution of N-(?-butoxycarbonyl)glycine (3.1 g, 1.0 eq) dissolved in TBME (12 mL) over 30 min. Stirring was continued for an additional 30 min, whereupon trans-4-hexen-l-ol (1.7 g, 0.95 eq) was added over 30 min. The mixture was maintained with stirring at 40 ¡ãC for an additional 3.5 h, then cooled to ambient temperature and stirred a further 14 h. The mixture was washed with IN HQ (2 x 7.8 mL) then water (1 x 7.8 mL). The organic layer was dried over a2S04, filtered and concentrated to give (.pound.)-hex-4-en-l-yl 2-((tert-butoxycarbonyl)amino)acetate as an oil. The oil was dissolved in DCM (12 mL) and 4.0 M HC1 in dioxane (2.8 mL) was added drop-wise. The mixture was stirred at ambient temperature for 1.5 h then the mixture was heated to 35 ¡ãC and stirred for 3 h. 4.0 M HC1 in dioxane (2.8 mL) was added drop-wise. After 6 h at 35 ¡ãC a further dose of 4.0 M HC1 in dioxane (2.8 mL) was added drop-wise and the mixture was stirred for a further 4 h. The mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. A portion of the residue (1.0 g) was dissolved in DCM (8 mL) and methyl 2-chloro-2-oxoacetate (0.63 g) was added. Triethylamine (1.0 g) was added drop-wise over 20 min. The mixture was stirred for 1 h before being quenched by IN HC1 (2.5 mL) to form a biphasic mixture. The layers were separated and the organic layer was washed with IN HCl (1 x 2.5 mL), water (1 x 2.5 mL) and concentrated under reduced pressure to provide an oil. Flash columnchromatography (S1O2, 10->60percent EtO Ac/Hex gradient) provided the title compound as an oil as a 95:5 mixture of trans:cis isomers. XH NMR (300 MHz, CDCI3) delta ppm 7.57 (s, 1 H), 5.31-5.55 (m, 2 H), 4.17 (t, J=6.69 Hz, 2 H), 4.12 (d, J=5.51 Hz, 2 H), 3.92 (s, 3 H), 1.97-2.10 (m, 2 H), 1.67-1.77 (m, 2 H), 1.62-1.67 (m, 3 H); 13C NMR (75 MHz, CDCI3) delta ppm 168.60, 160.35, 156.28, 129.49, 126.12, 65.34, 53.68, 41.47, 28.62, 28.17, 17.84; HRMS (M+H) m/z, calcd for CnH18N05, 244.1185; found 244.1 187.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,928-92-7, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; SISKO, Joseph; MANS, Douglas; YIN, Hao; WO2012/12391; (2012); A2;,
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Adding some certain compound to certain chemical reactions, such as: 928-92-7, name is 4-Hexen-1-ol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 928-92-7. 928-92-7

[199] To a vial charged with a stir bar were added tm -T-nonenoic acid (143.7 mg,0.9198 mmol), DMAP (23.0 mg, 0.184 mmol), EDC hydrochloride (352.1 rag, 1.840 mmol), and 7.5 mL dry’ dichloromethane under argon atmosphere. Trans-4-hexen-l-oi (216 pL, 1.840 mmol) was added, and the reaction ws stirred for 3 h. The reaction mixture was quenched with a solution of 1 M aq. HC1 (15 mL) after which, the product was extracted with DCM (4 x 15 mL). This organic phase was dried over MgSCL, filtered, and concentrated in vacuo. The product w’as purified by column chromatography (5:95 EtjO: pentane) to yield the product as a colorless oil (201.7 mg, 92% yield). 5H NMR (400 MHz, Chloroform-d)) d 5.52 – 5.36 (m, 4H), 4.08 (t, J~ 6.7 Hz, 2H), 2.31 (t, J- 7.5 Hz, 2H), 2.1 1 – 2.03 (m, 2H), 1.99 (dddd, J= 8.7, 6.5, 3.0, 1.3 Hz, 2H), 1.74 – 1.59 (m,1 OH), 1.42 – 1.26 (m, 4H).,3C NMR (101 MHz, CDCb) d 173.95, 131.28, 129.97, 125.81, 124.86, 63.78, 34.37, 32.39, 29.21, 28.88, 28.66, 28.47, 24.91, 17.94, 17.93.HRMS (EH-): [M] _ CisEbcCb Calculated – 238.1933, Found – 238.1935.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 928-92-7.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; AHMED, Tonia, S.; MONTGOMERY, Patrick, T.; GRUBBS, Robert, H.; (104 pag.)WO2019/113019; (2019); A2;,
Alcohol – Wikipedia,
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928-92-7, Adding a certain compound to certain chemical reactions, such as: 928-92-7, 4-Hexen-1-ol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 928-92-7, blongs to alcohols-buliding-blocks compound.

202] To a vial charged with a stir bar were added tram- 9 -¡¤ u n d e e e no i e acid (51.4 g,0,280 mmol), DMAP (6.8 mg, 0.0560 mmol), EDC hydrochloride (106.9 mg, 0.560 mmol), and 2.2 mL dry dich.oromethane under argon atmosphere. 7ram’-4~hexen-l-ol (65.6 pL, 0.560 mmol) was added, and the reaction was stirred for 3 h. The reaction mixture was quenched with a solution of 1M aq. HC1 (5 mL) after which, the product was extracted with DCM (4 x 5 mL). This organic phase was dried over MgS04, filtered, and concentrated in vacuo. The product was purified by column chromatography (5:95 Et20: pentane) to yield the product as a colorless oil (68.3 g, 92% yield).*H NMR (400 MHz, Chlorofomw/i) d 5.46 – 5.25 (m, 4H), 3.99 (t, 6.7 Hz, 2H), 2.27 – 2.15(m, 2H), 1.97 (tdd, J= 7.6, 5.9, 1.5 Hz, 2H), 1.92 – 1.85 (m, 2H), 1.65 – 1.49 (m, 10H), 1.32 – 1.13 (m, 8H).C NMR (101 MHz, CDCb) 6 174.12, 131.69, 130.10, 125.93, 124.76, 63.90, 34.53, 32.70, 29.66, 29.27, 29.26, 29.11, 29.02, 28.60, 25.15, 18.08, 18.06.HRMS (Hi -): [M]+ 7H30O2 Calculated – 266.2237, Found – 266.2246.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,928-92-7, its application will become more common.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; AHMED, Tonia, S.; MONTGOMERY, Patrick, T.; GRUBBS, Robert, H.; (104 pag.)WO2019/113019; (2019); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts