Tetrahydrofuran → 3-(Hexadecylthio)-1-propanol

HRID 248142Notes

Reaction equation

HRID 248142 reaction equation
[BH4-].[Li+].O1CCCC1.[CH2:8]([S:24][CH2:25][CH2:26][C:27](OCC)=[O:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>O>[CH2:8]([S:24][CH2:25][CH2:26][CH2:27][OH:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 19764352Ethyl 3-(hexadecylthio)propanoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a slurry of 147.4 mg of lithium borohydride in 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-4d31af5dd4444ba083c369ff0c102fa7
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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