Hydride → (4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-yl)methanol
Reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].S([O-])(O)(=O)=O.[K+]>O1CCCC1.C(OCC)C.C(OCC)(=O)C.CCCCCC>[F:18][C:17]([F:19])([F:20])[C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:3][OH:2])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (3.71 g, 13.3 mmol) in tetrahydro-furan (30 mL) is added lithium aluminum hydride (14.6 mmol, 1.0 M in tetrahydro-furan) at 0° C. under inert atmosphere of nitrogen. After the reaction is stirred at 0° C. for 10 minutes following completion of hydride addition, it is quenched with ethyl acetate (10 mL) followed by potassium hydrogen sulfate (1.0 M, 15 mmol) slowly at 0° C., diluted mixture with ethyl ether and filtered. Organic layers are washed with brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. Column chromatography (silica gel) with 20-80% ethyl acetate/hexane gradient gives 3.1 g (12.3 mmol, 93%) of title compound.
Workup
- customis quenched with ethyl acetate (10 mL)
- filtrationfiltered
- washOrganic layers are washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e050339234a34ae693afdbb2c4a23893
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989457B2
Reaction notes
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