Water → 3-(Hexadecylthio)-1-propanol

HRID 1885450Notes

Reaction equation

HRID 1885450 reaction equation
[BH4-].[Li+].[CH2:3]([S:19][CH2:20][CH2:21][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]([S:19][CH2:20][CH2:21][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 19764352Ethyl 3-(hexadecylthio)propanoate

Product 1

HCID 178317033-(Hexadecylthio)-1-propanolYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 147.4 mg of lithium borohydride in 20 ml of tetrahydrofuran is added 2.4 g of 3-(hexadecylthio)propanoic acid, ethyl ester. This mixture is refluxed overnight, poured into water and extracted with ethyl acetate, to give 2.1 g of the desired compound.

Workup

  1. temperatureThis mixture is refluxed overnight
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-491fdd64b67f4748a03d1352412f4a75
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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