Water → 2,2-Difluoro-3-phenylpropan-1-ol
Reaction equation
[F:1][C:2]([F:15])([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](OCC)=[O:4].[BH4-].[Na+].O>CO.C(OCC)(=O)C>[F:1][C:2]([F:15])([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][OH:4]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
To a cooled solution of Intermediate 90 (2.2 g, 10.3 mmol) in methanol (30 mL) was added sodium borohydride (1.94 g, 51 mmol). The mixture was stirred at 5° C. for 20 minutes and at room temperature for 2 hours. To the crude reaction was added water (1 mL) and the solvents reduced under reduced pressure. The residue was dissolved in ethyl acetate (50 mL) and washed with brine (2×25 mL), dried (Na2SO4), and concentrated. Purification by column chromatography with silica gel eluting with ethyl acetate/n-hexane 1:5 gave the title compound (0.75 g, 42%) as oil
Workup
- customTo the crude reaction
- washwashed with brine (2×25 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customPurification by column chromatography with silica gel eluting with ethyl acetate/n-hexane 1:5
Sources & evidence
- ORD record
- ord-8c84a11b34b34b8fb16774c6dd7d5779
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242177B2
Reaction notes
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