Diethyl Ether → 2-[(4-Chloro-2-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile
Reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[O:9])=[C:6]([F:17])[CH:5]=1.[Cl-].[NH4+].C(OCC)C>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([CH:8]([OH:9])[CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[C:6]([F:17])[CH:5]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
1.01 g (26.6 mmol) of sodium borohydride were added to 5.40 g (24.1 mmol) of the compound from Example 130A in 99 ml of ethanol and 25 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 45 minutes. The reaction mixture was added to saturated aqueous ammonium chloride solution and diethyl ether, the phases were separated, the aqueous phase was extracted twice with diethyl ether, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. 5.25 g (96% of theory) of a mixture of the diastereomers of the title compound were obtained.
Workup
- customthe phases were separated
- extractionthe aqueous phase was extracted twice with diethyl ether
- washthe combined organic phases were washed with saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- addition5.25 g (96% of theory) of a mixture of the diastereomers of the title compound
- customwere obtained
Sources & evidence
- ORD record
- ord-332b290c8150456fbefdeb171e877268
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Reaction notes
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