Reaktion #81138

Reaktionsgleichung

alcohol

tert-butyl (2RS, 3RS)-2-(3,4-dichlorobenzyl)-3-hydroxybutanoate

lithium borohydride

→

(2RS, 3RS)-2-(3,4-dichlorobenzyl)-1,3-butanediol

Ausbeute 90.0%

Lösungsmittel

ethyl ether

tetrahydrofuran

ethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturunder cooling with ice
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature for 3 hours
4. 4
   Waschenwashed with a saturated sodium chloride aqueous solution
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   SonstigeThe drying agent was separated by filtration
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Vorschrift

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.

Quelle