Water → alpha-(Butylthio)-alpha-(m-benzoylphenyl)propionitrile
Reaction equation
[CH2:1]([S:5][CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)[C:7]#[N:8])[CH2:2][CH2:3][CH3:4].[CH3:23][O-].[Na+].CI.O>CO>[CH2:1]([S:5][C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:10]=1)([CH3:23])[C:7]#[N:8])[CH2:2][CH2:3][CH3:4]Participants
Procedure
90 mg of alpha-(butylthio)(m-benzoylphenyl)-acetonitrile was dissolved in 1 ml of anhydrous methanol, and 0.15 ml of a 2.7 M methanol solution of sodium methoxide was added in an atmosphere of argon under ice cooling, followed by addition of 0.05 ml of methyl iodide. The temperature of the mixture was brought to room temperature, and the mixture was stirred for 30 minutes. Water (20 ml) was added, and the mixture was extracted with 20 ml of ether three times. The extract was washed with 10 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; benzene) to afford 82 mg (yield 87%) of alpha-(butylthio)-alpha-(m-benzoylphenyl)propionitrile as a colorless oil.
Workup
- customwas brought to room temperature
- extractionthe mixture was extracted with 20 ml of ether three times
- washThe extract was washed with 10 ml of water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography (silica gel; benzene)
Sources & evidence
- ORD record
- ord-0b9090e245ec4a68a0fbbf6c88debfe1
- Source dataset
- uspto-grants-1982_07
- Patent number
- US04340740
Reaction notes
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