Methyl iodide → N-methoxy-2-(2-(4-methoxyphenyl)cyclopropyl)-N-methylacetamide
Reaction equation
[CH2:1]([Zn]CC)C.IC.C(COC)OC.[CH3:14][O:15][N:16]([CH3:30])[C:17](=[O:29])[CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>ClCCl.O>[CH3:14][O:15][N:16]([CH3:30])[C:17](=[O:29])[CH2:18][CH:19]1[CH2:1][CH:20]1[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The solution of diethyl zinc in hexanes (1M, 17.4 mL, 17.4 mmol) was added slowly to the mixture of iodomethane (2.5 mL, 34.9 mmol), dimethoxy ethane (1.82 mL) in dichloromethane (25 mL) at −15° C. After stirring for 20 minutes, the solution of (E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamide (558) (2.0 g, 8.7 mmol) in dichloromethane (10 mL) was added to the reaction mixture. The resulting mixture was allowed to warm to room temperature over 24 hours. The reaction mixture was diluted with water and extracted with dichloromethane. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (30% EtOAc in hexanes) to provide N-methoxy-2-(2-(4-methoxyphenyl)cyclopropyl)-N-methylacetamide (559) (1.8 g, 85.2%) as a yellow oil.
Workup
- extractionextracted with dichloromethane
- washThe organic phase was washed with water, brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography on silica gel (30% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-84260d29c80941ffaec416777ff2901c
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476308B2
Reaction notes
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