Dimethyl Sulfoxide → 1-Methylbicyclo[2.2.1]heptan-2-one

To a solution of oxalyl dichloride (31.75 g, 0.25 mol) in DCM (300 mL) was added at −78° C. in consecutive order DMSO (19.5 g, 0.25 mol), a solution of 1-methylbicyclo[2.2.1]heptan-2-ol (21 g, 0.167 mol) in DCM (50 mL) and then triethylamine (50 g, 0.5 mol). The mixture was stirred at room temperature overnight and then poured into 200 mL, water. The resulting mixture was extracted with DCM (2×100 mL). The combined extracts were washed with saturated aqueous sodium bicarbonate solution (50 mL), brine (50 mL) and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave crude methylbicyclo[2.2.1]heptan-2-one, which was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether) to afford 12.4 g (0.10 mol, yield: 60%) of this compound.

1. extractionThe resulting mixture was extracted with DCM (2×100 mL)
2. washThe combined extracts were washed with saturated aqueous sodium bicarbonate solution (50 mL), brine (50 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationConcentration under reduced pressure

ORD record

ord-b08b6f0cde6a4c41a087cfabd9786c57

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139534B2