Hydrochloric Acid → 4-methyl-4-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one
Reaction equation
CON(C)[C:4](=[O:22])[C:5]([CH3:21])([C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][N:14]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH:24]([Mg]Br)=[CH2:25].Cl>O1CCCC1>[CH3:21][C:5]([C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][N:14]=1)([CH2:6][CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1)[C:4](=[O:22])[CH:24]=[CH2:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of N-methoxy-N,2-dimethyl-2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide (401 mg) in tetrahydrofuran (4.8 mL) was cooled to 0° C., and vinylmagnesium bromide (1.0M tetrahydrofuran solution, 4.76 mL) was added dropwise thereto. The reaction mixture was stirred at room temperature for 3 hr, and poured into 1M hydrochloric acid, and the mixture was stirred for 30 min. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (250 mg, yield 69%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).
Workup
- stirringthe mixture was stirred for 30 min
- extractionThe reaction mixture was extracted with ethyl acetate
- washthe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-baac38781a9c4e61a618b92ffe6caeb9
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318746B2
Reaction notes
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