Dimethylformamide → 4-(4-Fluorophenyl)-4-methoxy-1-phenylcyclohexanecarbonitrile
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:22])[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:23]N(C=O)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([O:22][CH3:23])[CH2:13][CH2:12][C:11]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1Participants
3
Procedure
300 mg of 4-(4-fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile were dissolved in 2.5 ml of dry DMF in a flask which had been dried and flushed with argon, treated under argon with 73 mg of sodium hydride (80% strength in mineral oil) and stirred for 30 min at room temperature. Subsequently, 0.14 ml of iodomethane was slowly added dropwise under argon. The reaction mixture was stirred for 3 h, then treated with water and extracted with EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. The crude product, a brown oil, was purified by chromatography on silica gel using HEP/EA (2:1). 290 mg of the title compound were obtained as a white amorphous solid.
Workup
- customhad been dried
- customflushed with argon
- additiontreated under argon with 73 mg of sodium hydride (80% strength in mineral oil)
- additionSubsequently, 0.14 ml of iodomethane was slowly added dropwise under argon
- stirringThe reaction mixture was stirred for 3 h
- additiontreated with water
- extractionextracted with EA
- dry with materialThe combined organic phases were dried over magnesium sulfate
- customthe solvent was removed in vacuo
- customThe crude product, a brown oil, was purified by chromatography on silica gel using HEP/EA (2:1)
Sources & evidence
- ORD record
- ord-45e5bacc892f42a29835eba6ca64acec
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076324B2
Reaction notes
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