HRID248167

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID4148881

Lithium borohydride

BH4Li

结构：CCCCCCCCCCCCCCCCOCC(CSCCCCCCCCCCCCCCCC)C(=O)OCC

HCID19764340

未命名化合物

PRODUCTS

生成物

结构：CCCCCCCCCCCCCCCCOCC(CO)CSCCCCCCCCCCCCCCCC

HCID19764327

未命名化合物

收率 68.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

To a slurry of 1.04 g of lithium borohydride in tetrahydrofuran at ambient temperature is added 29 g of ethyl 3-(hexadecyloxy)-2-[(hexadecylthio)methyl]propanoate followed by heating at reflux for 18 hours. The mixture is poured into water containing a small amount of acid followed by extraction with ether to give after drying and evaporation, a residue which is columned on silica gel using 30:1 hexane:ethyl acetate. Fractions containing the product are evaporated to give 18.4 g of the desired product.

WORKUP

后处理

temperatureby heating
temperatureat reflux for 18 hours
extractionfollowed by extraction with ether
customto give
customafter drying
customevaporation
additionFractions containing the product
customare evaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d8b570829fa441559ec8c2e3fe9e9268
来源数据集: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05208223
来源说明: uspto-grants-1993_05

反应 SMILES

[BH4-].[Li+].[CH2:3]([O:19][CH2:20][CH:21]([CH2:27][S:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:22](OCC)=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O>O1CCCC1>[CH2:3]([O:19][CH2:20][CH:21]([CH2:27][S:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:22][OH:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]