Dimethyl Sulfoxide → HCID 69429952, compound

Participants

Reaction Steps

2.37 g (18.7 mmol) of oxalyl chloride and 2.92 g (37.3 mmol) of DMSO were dissolved in 10 ml of dichloromethane at −78° C. After stirring for one hour, 2.00 g (9.33 mmol) of 3,3-diphenyl-1-propanol was added to the obtained solution at that temperature, and they were stirred for additional 2 hours. 5.66 g (56.0 mmol) of triethylamine was added to the obtained mixture and they were stirred for one hour while the temperature was returned to room temperature. After the dilution with dichloromethane followed by the washing with saturated aqueous sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue thus obtained was added to a THF solution obtained by stirring 2.67 g (11.9 mmol) of ethyl diethylphosphonoacetate and 596 mg (14.9 mmol) of sodium hydride (60% oily) under cooling with ice for one hour. They were stirred at room temperature for 2 hours. After the dilution with ethyl acetate followed by the washing with saturated aqueous sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue thus obtained was purified by the silica gel chromatography (hexane/ethyl acetate=5/1 to 3/1) to obtain the title compound.

Provenance & Evidence