Sodium borohydride → HCID 22262008, compound

HRID 1610697Notes

Reaction equation

HRID 1610697 reaction equation
[F:1][C:2]([F:15])([CH:12]([F:14])[F:13])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1)=[O:4].[BH4-].[Na+]>CO.O>[F:1][C:2]([F:15])([CH:12]([F:13])[F:14])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1)[OH:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22261503HCID 22261503, compound

Product 1

HCID 22262008HCID 22262008, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2,2,3,3-tetrafluoro-1-(3-methylphenyl)propane-1-one (9.11 g, 41.4 mmol) in methanol (50 ml) was added sodium borohydride (0.76 g, 20 mmol) by small portions under ice-cooling and the mixture was stirred at room temperature for 1 hr. The reaction solution was diluted with water, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-3/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-3/1)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-d744a5e666d042dca80f4374f94cf972
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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