Water → 3-(Hexadecyloxy)-2-(hexadecylthio)methyl-1-propanol

HRID 248140Notes

Reaction equation

HRID 248140 reaction equation
[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]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 19764340Ethyl 3-(hexadecyloxy)-2-[(hexadecylthio)methyl]propanoate

Product 1

HCID 197643273-(Hexadecyloxy)-2-(hexadecylthio)methyl-1-propanolYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 1.04 g of lithium borohydride in 20 ml of tetrahydrofuran is added 29 g of 3-(hexadecyl-oxy)-2-[(hexadecylthio)methyl]propanoic acid, ethyl ester. This mixture is refluxed overnight, poured into water and purified by chromatography on silica gel [hexane:ethyl acetate (30:1)], to give 18.4 g of the desired compound.

Workup

  1. temperatureThis mixture is refluxed overnight
  2. custompurified by chromatography on silica gel [hexane:ethyl acetate (30:1)]

Sources & evidence

ORD record
ord-86fdf7ae4c794f358f3ce83b02b15984
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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