Antimony trichloride → 2-[3-[4-[(Fluoromethyl)thio]phenyl]-1-benzofuran-5-yl]-5-methyl-1,3,4-oxadiazole

To a solution of [bis(2-methoxyethyl)amino]sulfur trifluoride (1.38 mL, 7.50 mmol) in dichloromethane (10 mL) was added dropwise a solution of 2-methyl-5-[3-[4-(methylthio)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole (1.61 g, 5.00 mmol) in dichloromethane (15 mL) at room temperature. Antimony (III) chloride (0.0570 g, 0.250 mmol) was added to the solution, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/tetrahydrofuran=1/1) and recrystallized from hexane/ethyl acetate to give the title compound (517 mg, yield 30%) as pale-yellow crystals.

1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
2. dry with materialdried over anhydrous magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe residue was purified by silica gel column chromatography (hexane/tetrahydrofuran=1/1)
5. customrecrystallized from hexane/ethyl acetate

ORD 기록

ord-f89e108746f840ab95f83b7d38c22bb8

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08492378B2