Hydrochloric Acid → 4-[3-fluoro-4-(methylsulfanyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

A solution of 2-[3-fluoro-4-(methylsulfanyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (1.33 g) in tetrahydrofuran (15.6 mL) was cooled to 0° C., and vinylmagnesium bromide (1.0M tetrahydrofuran solution, 15.6 mL) was added dropwise thereto. The reaction mixture was stirred at room temperature for 4 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 (1.12 g, yield 93%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio).

1. stirringthe mixture was stirred for 30 min
2. extractionThe reaction mixture was extracted with ethyl acetate
3. washthe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated

ORD record

ord-1cde774d4b084f63ae229278d8b1fd14

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318746B2