Lithium borohydride → (2RS,3RS)-2-(3,4-dichlorobenzyl)-1,3-butanediol

HRID 376189Notes

Reaction equation

HRID 376189 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][CH:6]([CH:14]([OH:16])[CH3:15])[C:7](OC(C)(C)C)=[O:8].[BH4-].[Li+]>C(OCC)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][CH:6]([CH:14]([OH:16])[CH3:15])[CH2:7][OH:8]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 53695590tert-butyl (2RS,3RS)-2-(3,4-dichlorobenzyl)-3-hydroxybutanoate

Product 1

HCID 19073701(2RS,3RS)-2-(3,4-dichlorobenzyl)-1,3-butanediolYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g of the alcohol compound thus obtained was dissolved in a liquid mixture of 30 ml of ethyl ether and 30 ml of tetrahydrofuran, and 1.2 g of lithium borohydride was added thereto with stirring under cooling with ice. The mixture was stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl ether, then washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain 2.1 g (yield: 90%) of (2RS, 3RS)-2-(3,4-dichlorobenzyl)-1,3-butanediol.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringThe mixture was stirred at room temperature for 3 hours
  4. washwashed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe drying agent was separated by filtration
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4a8d27a50a63458d9c6b3f81853d1b1d
Source dataset
uspto-grants-1996_01
Patent number
US05488149

Reaction notes

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