Dimethyl Sulfoxide → HCID 59463783, compound

Participants

Reaction Steps

To a chilled (−60° C.) solution of 0.31 mL (3.5 mmol) of oxalyl chloride in 5 μL of methylene chloride was added a solution of 0.5 mL (7 mmol) of DMSO in 2.5 mL of dichloromethane. After 10 minutes, a solution of 0.42 g (1.76 mmol) of 2-(4-methyl-6-methylsulfanylchroman-4-yl)ethanol in 2.5 mL of dichloromethane was added. The mixture stirred for 15 minutes and then 1.5 mL (10.6 mmol) of triethylamine was added. The reaction was warmed at 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 0.4 g (94%) of (4-methyl-6-methylsulfanylchroman-4-yl)acetaldehyde as an oil.

Provenance & Evidence