Dimethyl Sulfoxide → 4-Methyloxane-4-carbaldehyde

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Reaction Steps

Oxalyl chloride (0.419 mL, 4.80 mmol) was dissolved in dichloromethane (7.5 mL). To this, dimethyl sulfoxide (0.409 mL, 5.76 mmol) was added dropwise under a nitrogen atmosphere at −78° C. and the mixture was stirred for 15 minutes. To this, a dichloromethane solution (2.5 mL) of (4-methyltetrahydro-2H-pyran-4-yl)methanol (250 mg, 1.92 mmol) synthesized according to the method described in WO 08/029,825 was added at the same temperature and the mixture was stirred for 1 hour. To this, triethylamine (1.34 mL, 9.60 mmol) was added and the mixture was stirred at a temperature of −78° C. to room temperature for 1.2 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1) to give 4-methyltetrahydro-2H-pyran-4-carbaldehyde (173 mg, yield: 70%).

Provenance & Evidence