Water → [3-Fluoro-4-(methylsulfanyl)phenyl]methanol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10][CH3:11])[CH:5]=[O:6].[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[S:10][CH3:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The mixture of 3-fluoro-4-(methylsulfanyl)benzaldehyde (19.44 g, 114.2 mmol) and sodium borohydride (2.1 g, 55.46 mmol) in methanol (200 mL) was stirred at room temperature for 2 hour. Water was added to the mixture, and the mixture was evaporated, diluted with ethyl acetate (300 mL), washed with water (100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/4) to provide the subtitle compound (19.91 g, 100% yield) as an oil.
Workup
- customthe mixture was evaporated
- additiondiluted with ethyl acetate (300 mL)
- washwashed with water (100 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/4)
Sources & evidence
- ORD record
- ord-eed3113a6cec47438bacb51ab499900f
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727238B2
Reaction notes
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