Sodium borohydride → 1-(4-Chloro-3-(methylsulfonyl)phenyl)ethanol

HRID 1845144Notes

Reaction equation

HRID 1845144 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11]([CH3:14])(=[O:13])=[O:12].[BH4-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[S:11]([CH3:14])(=[O:12])=[O:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 581882281-(4-Chloro-3-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 581879811-(4-Chloro-3-(methylsulfonyl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask was charged with 1-(4-chloro-3-(methylsulfonyl)phenyl)ethanone (12.0 g, 50.0 mmol) and tetrahydrofuran (100 mL) at 0° C. Sodium borohydride (3.7 g, 100 mmol) was added in portions and the reaction was stirred for 12 h at room temperature. The reaction was quenched with ice and extracted with MTBE. The organic solvents were removed under reduced pressure and the residue was purified by flash chromatography to get the title compound.

Workup

  1. customThe reaction was quenched with ice
  2. extractionextracted with MTBE
  3. customThe organic solvents were removed under reduced pressure
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-04c9c3ac5a06490b9bbfb2cb5b8cfa06
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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