Adding a certain compound to certain chemical reactions, such as: 23377-40-4, 3-(Hexadecyloxy)propan-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, 23377-40-4, blongs to alcohols-buliding-blocks compound. 23377-40-4
3-(Hexadecyloxy)propan-1-ol was synthesized in one step according to the method ofYamano, Y. et al., Biorg. Med. Chem. (2012) 20:3658-3665 and recrystallized from hexane. The crystalline product (200mg, 0.67mmol) was dissolved in dry CH2C12 and diisopropylethylamine (0.70 mL, 2.68 mmol, 4 equiv) was added while stirring at RT. 2- Cyanoethyloxy(N,N-diisopropylamino) phosphonamidic chloride (0. l8mL, 0.8mmol, 1.2 eq) was added dropwise and the solution was stirred for 45mm. After completion lSmL of CH2C12 were added and the organic phase was washed with saturated aqueous NaHCO3 anddried over MgSO4. The crude product was purified on a silica column with Hex:EtOAc:NEt350:50:1 as eluent to afford the title compound as a colorless liquid (175mg, 52% yield). Rf inEtOAc =0.28. MS (ESI): found 501 (M+H); mass expected for (C28H57N203P + H = 501.4).?H NMR (400 MHz, CDC13) 0.89 (t, J=6.85 Hz, 3H, CH3CH2) 1.19 (dd, J=6.72, 3.42 Hz,12H, 2 (CH3)2CHN) 1.26 (s, 26 H, 13 (Cl2)11) 1.56 (quin, J=6.94 Hz, 2H, OCH2CH2CH2)1.88 (quin, J=6.30 Hz, 2H, POCH2CH2CH2O) 2.64 (t, J6.60 Hz, 2H, CH2CN) 3.40 (t,J=6.66 Hz, 2H, OC1j2CH2CH2) 3.50 (t, J=6.30 Hz, 2H, POCH2CH2CLLaO) 3.54 – 3.65 (m,2H, 2 CH) 3.65 – 3.79 (m, 2H, POC1j2CH2CH2O) 3.79 – 3.93 ppm (m, 2H, POCH2CH2CN).?3C NMR (101 MHz, CDC13) oe 14.1 (s, 1C, CH3CH2) 20.3 (d, J6.60 Hz, 1C, CH2CN) 22.7(s, 1C, CH2CH2CH3) 24.5 and 24.63 (2 d, J=7.70 Hz, 2x2C, (CH3)2CHN) 26.2 (s, 1C,OCH2CH2CH2) 29.3 (s, 1CH211) 29.5 (s, 1CH211) 29.6 (s, 2CH211) 29.6 (s, 1CH211) 29.7 (s,5CH211) 29.8 (s, 1CH211) 31.5 (d,J7.34 Hz, 1C, POCH2CH2CH2O) 31.9 (s, 1CH211) 43.0 (d,J=1 1.74 Hz, 2C, 2 CH) 58.3 (d, J=19.07 Hz, 1C, POCH2CH2CN) 60.7 (d, J17.61 Hz, 1C,POCH2CH2CH2O) 67.3 (s, 1C, POCH2CH2CH2O) 71.1 (s, 1C, OCH2CH2CH2), 117.6 ppm (s,1C, CN). 3?P NMR (162 MHz, CDC13, ?H-decoupled) 8 147.56 ppm (s).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23377-40-4, its application will become more common.
Reference:
Patent; UNIVERSITY OF MASSACHUSETTS; UNIVERSITY OF SOUTHAMPTON; WATTS, Jonathan; HAITCHI, Hans, Michael; PENDERGRAFF, Hannah; (88 pag.)WO2018/226788; (2018); A1;,
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