Dimethyl Sulfoxide → HCID 59463779, compound

Participants

Reaction Steps

To a chilled (−60° C.) solution of 0.254 mL (2.9 mmol) of oxalyl chloride in 5 mL of methylene chloride was added a solution of 0.414 mL (7 mmol) of DMSO in 2.5 mL of dichloromethane. After 10 minutes, a solution of 450 mg (1.46 mmol) of 1,1,1-trifluoro-3-(4-methyl-6-methylsulfanylchroman-4-yl)propan-2-ol in 2.5 mL of dichloromethane was added. The mixture stirred for 15 minuets and then 1.2 mL (8.7 mmol) of triethylamine was added. The reaction was warmed to room temperature for 30 minutes and then concentrated in vacuo. The residue was diluted with water and extracted with diethyl ether. The combined organic fractions were washed with four portions of water, once with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 340 mg (94%) of 1,1,1-trifluoro-3-(4-methyl-6-methylsulfanylchroman-4-yl)propan-2-one as an oil.

Provenance & Evidence