Extracurricular laboratory: Synthetic route of tert-Butyl 3-hydroxypent-4-enoate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,122763-67-1, its application will become more common.

Related Products of 122763-67-1 ,Some common heterocyclic compound, 122763-67-1, molecular formula is C9H16O3, 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.

Vinyl acetate (15.6mL, 169.6mmol) was added to a solution of 1 (9.75g, 56.7mmol) in pentane (120mL). Amano lipase (from Burkholderia cepacia (6.2g) and MS 4 (8.9g) were added and the suspension was stirred at 30C for 16h. The reaction mixture was monitored by TLC. The lipase and sieves were filtered and washed with Et2O. The solvent was removed and the crude product was purified by silica gel column chromatography (EtOAc/Petroleum ether 1:9) to afford 1 (R) (4.4g, 25.6mmol, 45%) and 3 (S) (5.1g, 23.8mmol, 42%). 1 (R): [alpha]20D=+4.1 (c=1.04, CHCl3). 1H NMR (250MHz, CDCl3): delta=5.83 (ddd, J=16.0, 10.5, 5.5Hz, 1H, CH=CHaHb), 5.25 (dt, J=17.2, 1.5Hz, 1H, CH=CHaHb), 5.09 (dt, J=10.5, 1.4Hz, 1H, CH=CHaHb), 4.45 (m, 1H, CHOH), 3.2 (br s, 1H, CHOH), 2.47 (dd, J=16.1, 4.7Hz, 1H, COCHaHb), 2.38 (dd, J=16.1, 7.7Hz, 1H, COCHaHb), 1.42 (s, 9H, t-Bu) ppm. 13C NMR (62.5MHz, CDCl3): delta=171.7, 139.0, 115.2, 81.4, 69.1, 42.2, 28.1ppm. IR (film): numax=3434, 2979, 2931, 1726, 1645, 1393, 1368, 1256, 1157, 1039, 993, 924, 842, 763cm-1. HRMS (ESI): calcd for C9H16O3 [M+Na]+ 195.0997 found 195.1002. 3 (S): [alpha]20D=-5.5 (c=1.09, CHCl3). 1H NMR (250MHz, CDCl3): delta=5.81 (ddd, J=17.0, 10.5, 6.2Hz, 1H, CH=CHaHb), 5.59 (m, 1H, CHOCOCH3), 5.28 (dt, J=17.2, 1.2Hz, 1H, CH=CHaHb), 5.18 (dt, J=10.5, 1.2Hz, 1H, CH=CHaHb), 2.60 (dd, J=15.3, 7.9Hz, 1H, tBuOCOCHaHb), 2.50 (dd, J=15.3, 5.9Hz, 1H, tBuOCOCHaHb), 2.04 (s, 3H, OCOCH3), 1.42 (s, 9H, t-Bu) ppm. 13C NMR (62.5MHz, CDCl3): delta=169.9, 169.1, 135.3, 117.4, 81.2, 71.2, 40.8, 28.1, 21.2ppm. IR (film): numax=2979, 2933, 1736, 1646, 1457, 1369, 1290, 1235, 1159, 1024, 991, 947, 847, 764cm-1. HRMS (ESI): calcd for C11H18O4 [M+Na]+ 237.1103 found 237.1109.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,122763-67-1, its application will become more common.

Reference:
Article; Menhour, Boudjema; Akong, Firmin Obounou; Mayon, Patrick; Ple, Karen; Bouquillon, Sandrine; Dorey, Stephan; Clement, Christophe; Deleu, Magali; Harakat, Dominique; Haudrechy, Arnaud; Tetrahedron; vol. 72; 47; (2016); p. 7488 – 7495;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

New downstream synthetic route of 122763-67-1

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. 122763-67-1, tert-Butyl 3-hydroxypent-4-enoate, other downstream synthetic routes, hurry up and to see.

Electric Literature of 122763-67-1, Adding some certain compound to certain chemical reactions, such as: 122763-67-1, name is tert-Butyl 3-hydroxypent-4-enoate,molecular formula is C9H16O3, 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 122763-67-1.

[0216] To a solution of tert-butyl 3-hydroxypent-4-enoate, XL VI (674 mg, 3.92 mmol) in DCM (15 mL) was added diisopropylallylboronate XLV(2 g, 11.76 mmol) via syringe. To the mixture was then added Grubbs’ first generation catalyst (260 mg, 0.31 mmol, 7.5 mol%) and the vessel was purged with argon. The reaction was heated at 65 C under nitrogen for 18h. The mixture was concentrated under vacuum and the residue was purified by flash column chromatography (100% hexane?30% EtOAc/hexane) to afford tert-butyl 2-(2- hydroxy-3,6-dihydro-2H-l,2-oxaborinin-6-yl)acetate XL VII (770 mg, 3.63 mmol, 92.7% yield).

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. 122763-67-1, tert-Butyl 3-hydroxypent-4-enoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; REMPEX PHARMACEUTICALS, INC.; DUDLEY, Michael, N.; HECKER, Scott; RODNY, Olga; WO2013/122888; (2013); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

New downstream synthetic route of 122763-67-1

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. 122763-67-1, tert-Butyl 3-hydroxypent-4-enoate, other downstream synthetic routes, hurry up and to see.

Electric Literature of 122763-67-1, Adding some certain compound to certain chemical reactions, such as: 122763-67-1, name is tert-Butyl 3-hydroxypent-4-enoate,molecular formula is C9H16O3, 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 122763-67-1.

[0216] To a solution of tert-butyl 3-hydroxypent-4-enoate, XL VI (674 mg, 3.92 mmol) in DCM (15 mL) was added diisopropylallylboronate XLV(2 g, 11.76 mmol) via syringe. To the mixture was then added Grubbs’ first generation catalyst (260 mg, 0.31 mmol, 7.5 mol%) and the vessel was purged with argon. The reaction was heated at 65 C under nitrogen for 18h. The mixture was concentrated under vacuum and the residue was purified by flash column chromatography (100% hexane?30% EtOAc/hexane) to afford tert-butyl 2-(2- hydroxy-3,6-dihydro-2H-l,2-oxaborinin-6-yl)acetate XL VII (770 mg, 3.63 mmol, 92.7% yield).

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. 122763-67-1, tert-Butyl 3-hydroxypent-4-enoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; REMPEX PHARMACEUTICALS, INC.; DUDLEY, Michael, N.; HECKER, Scott; RODNY, Olga; WO2013/122888; (2013); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Share a compound : 122763-67-1

The synthetic route of 122763-67-1 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 122763-67-1, name is tert-Butyl 3-hydroxypent-4-enoate, the common compound, a new synthetic route is introduced below. SDS of cas: 122763-67-1

EXAMPLE 12 – Preparation of compound 52- 5-Methoxymethoxy-pent-l-ene-3-ol (Scheme 10)Compound 48 (100 g) is reduced to the corresponding alcohol using lithium aluminum hydride as described by Batt, et al. (Eur. J. Org. Chem., 2011, 6039-6055). The resulting diol (13 g, 1 eq.) is added to a mixture of cyclohexane (26 mL), dichloromethane (DCM, 13 mL) and diisopropyl ethylamine (DIEA, 18 g, 1.1 eq.) under nitrogen. Methoxymethyl chloride (1 eq.) is added dropwise and the reaction is stirred at 20 deg C for 12 hours. DCM (100 mL) is then added and the mixture is washed with aqueous hydrochloric acid (2 M, 30 mL) and saturated aqueous sodium bicarbonate (2 x 30 mL). The organic phase is dried over anhydrous sodium sulfate, is filtered and is concentrated to dryness. The residue is purified on silica gel (10% ethyl acetate/hexane) giving the primary MOM ether (compound 52, 4 g) as a yellow oil. 1H NMR (300 MHz, CDCI3): 6 1.75-1.95 (m, 2H), 3.35 (s, 3H), 3.65-3.80 (m, 2H), 4.30-4.35 (m, 1H), 4.65 (s, 2H), 5.10-5.15 (m, 1H), 5.25-5.30 (m, 1H), 5.85-5.95 (m, 1H).

The synthetic route of 122763-67-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PREVACUS, INC.; LEVY, Daniel, E.; (110 pag.)WO2016/44559; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts