Hydrochloric Acid → 1-[1-(4-Chlorophenyl)cyclopropyl]ethan-1-one
Reaction equation
Cl[C:2]1C=CC(C2(C#N)CC2)=C[CH:3]=1.C[Mg]Cl.[O:16]1[CH2:20][CH2:19]CC1.[ClH:21].[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[Cl:21][C:25]1[CH:26]=[CH:27][C:22]([C:28]2([C:20](=[O:16])[CH3:19])[CH2:3][CH2:2]2)=[CH:23][CH:24]=1Participants
Procedure
To a solution of 1-(4-chlorophenyl)-1-cyclopropanecarbonitrile (181 mg, 1.0 mmol) in toluene (5 mL) was added drop wise at 20° C. under an atmosphere of nitrogen a 3 M solution of methylmagnesium chloride in tetrahydrofuran (0.5 mL, 1.5 mmol). The reaction was heated for 16 h to 80° C. In an ice bath 6 N aqueous hydrochloric acid solution (1.08 mL) was added carefully and the reaction was heated to reflux for 2 h. The reaction was diluted with toluene, extracted once with water, once with brine, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using heptane/ethyl acetate (9:1 v/v) as eluent to yield the title compound (67 mg, 34%) as a yellow oil.
Workup
- temperatureThe reaction was heated for 16 h to 80° C
- temperaturethe reaction was heated
- temperatureto reflux for 2 h
- extractionextracted once with water, once with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-76d347f529674496ae0c0fe736904a84
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962834B2
Reaction notes
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