Synthetic Route of 23377-40-4, 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.23377-40-4, name is 3-(Hexadecyloxy)propan-1-ol, molecular formula is C19H40O2, molecular weight is 300.52, as common compound, the synthetic route is as follows.
Compound 315: To a solution of 1H-tetrazole (0.415 g, 5.92 mmol) in 25 ml ether and 10 ml acetonitrile diisopropylamine (0.93 ml, 0.726 g, 7.03 mmol) was added. The precipitate was filtered off, washed with ether and dried under vacuum to give diisopropylammonium tetrazolide.Compound 316: 3-(hexadecyloxy)propan-1-ol (0.301 g, 1.00 mmol) and diisopropylammonium tetrazolide (0.115 g, 0.67 mmol) were coevaporated with DCM-AcCN mixture(10:10) 3 times. Dried mixture was dissolved in 7 ml DCM and added 3- ((bis(diisopropylamino)phosphino)oxy)propanenitrile (0.673 ml, 2.120 mmol). After 1 hour stirring at room temperature 1 ml methanol was added and stirred for 15 minutes. Then reaction was concentrated under vacuum; diluted with 10%TEA solution in EtOAc (100 ml) and washed with 10%NaHCO3 solution (2 x 50 ml) and water (2 x 50 ml); dried over anhydrous MgSO4; filtered off and evaporated. The crude product was purified with column chromatography using Hexanes:EtOAc:TEA (10:4:0.5). 1H-NMR: 3.89-3.54 (m, 6H); 3.49 (t, 2H, J=6.4 Hz); 3.39 (t, 2H, J=6.4Hz); 2.63 (dt, 2H, J=1.6, 6.4 Hz); 1.89-1.83 (m, 1H); 1.57-1.51 (m, 1H); 1.24 (s, 24H); 1.19-1.16 (m, 16H); 0.87 (t, 3H, J=6.4 Hz).
The chemical industry reduces the impact on the environment during synthesis 23377-40-4, I believe this compound will play a more active role in future production and life.
Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis, C.; PAINTER, George, R.; BLUEMLING, Gregory, R.; DE LA ROSA, Abel; (408 pag.)WO2016/145142; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts