Sodium borohydride → 3-(5-Trifluoromethylbenzofur-7-yl)-2-butanol

HRID 1824970Notes

Reaction equation

HRID 1824970 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:12]([CH3:16])[C:13](=[O:15])[CH3:14])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.[BH4-].[Na+]>C(O)C>[F:17][C:2]([F:1])([F:18])[C:3]1[CH:4]=[C:5]([CH:12]([CH3:16])[CH:13]([OH:15])[CH3:14])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 221449223-(5-Trifluoromethylbenzofur-7-yl)-2-butanone

Product 1

HCID 221448643-(5-Trifluoromethylbenzofur-7-yl)-2-butanolYield 45.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.09 gm (0.35 mMol) 3-(5-trifluoromethylbenzofur-7-yl)-2-butanone in ethanol was cooled to 0° C. To this solution was added 0.013 gm (0.35 mMol) sodium borohydride and the resulting mixture stirred for 30 minutes. The reaction mixture was then allowed to warm to room temperature and was concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed sequentially with 0.1 N hydrochloric acid, water, and saturated aqueous sodium chloride. The remaining organic phase was concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with 30% ethyl acetate in hexane. Fractions containing product were combined and concentrated under reduced pressure to provide 0.041 gm (45%) of the desired compound.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. washwashed sequentially with 0.1 N hydrochloric acid, water, and saturated aqueous sodium chloride
  3. concentrationThe remaining organic phase was concentrated under reduced pressure
  4. washeluting with 30% ethyl acetate in hexane
  5. additionFractions containing product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d44e87683e240ccb6b7652de52247e5
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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