(Dimethyl sulfide)trihydroboron → 2-(2-Fluorophenyl)-2-methylpropan-1-ol
Reaction equation
B.CSC.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([CH3:17])([CH3:16])[C:13](O)=[O:14]>C1COCC1>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([CH3:17])([CH3:16])[CH2:13][OH:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
Borane-methyl sulfide (2M in THF, 12.35 mL) was added dropwise to a solution of 2-(2-fluorophenyl)-2-methylpropanoic acid (example 90, step c) (1.5 g) in THF (30 mL). The reaction mixture was stirred at 20° C. for 8 hours. The mixture was quenched by careful addition of methanol until evolution of gas ceased. The solvents were removed under reduced pressure and the residue azeotroped with toluene. The crude product was purified by flash silica chromatography using 30% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.3 g.
Workup
- customThe mixture was quenched by careful addition of methanol until evolution of gas
- customThe solvents were removed under reduced pressure
- customthe residue azeotroped with toluene
- customThe crude product was purified by flash silica chromatography
- customPure fractions were evaporated to dryness
Sources & evidence
- ORD record
- ord-e53efcb7141c44a58f2ecee02677cf88
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148373B2
Reaction notes
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