Diethyl Ether → 2-[(4-Chlorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile
Reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH:12]2[CH2:14][CH:13]2[C:15]#[N:16])=[O:11])=[CH:6][CH:5]=1.[Cl-].[NH4+].C(OCC)C>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:11])[CH:12]2[CH2:14][CH:13]2[C:15]#[N:16])=[CH:8][CH:9]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
736 mg (19.5 mmol) of sodium borohydride were added to 4.85 g (17.7 mmol) of the compound from Example 74A in 73 ml of ethanol and 18 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. 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. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethanol 9/1) to result in 2.79 g (76% of theory) of a mixture of the diastereomers of the title compound.
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
- customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethanol 9/1)
Sources & evidence
- ORD record
- ord-94e859c622344289bde08b0eb8486043
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Reaction notes
Loading…