Methanol → HCID 54158845, compound

Participants

Reaction Steps

p-Dimethylaminobenzaldehyde (12.953 g) was dissolved in 30 ml of tetrahydrofuran, and 18.428 g of FAMSO and 12 ml of a 40% methanol solution of trimethylbenzylammonium hydroxide were added. The mixture was heated under reflux for 40 hours. Water was added, and the reaction mixture was acidified with acetic acid and then extracted with methylene chloride. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using methylene chloride/ethyl acetate as an eluant, and then recrystallized from diethyl ether to afford 13.492 g of 1-methylsulfinyl-1-methylthio-2-(p-dimethylaminophenyl)ethylene.

Provenance & Evidence