Triethylamine → 1-[(4-Methylphenyl)sulfonyl] 2-pyrrolidinecarboxaldehyde

Participants

Reaction Steps

To a mixture of 8.64 g of 1-[(4-methylphenyl)sulfonyl] 2-pyrrolidinemethanol and 14.2 ml of triethylamine in 100 ml of dry methyl sulfoxide is added slowly a solution of 16.16 g of sulfur trioxide pyridine complex in 100 ml of dry methyl sulfoxide. The solution is stirred at room temperature for one hour, then poured onto 1 l of ice water. The mixture is extracted with ethyl acetate. The combined organic extracts are washed with 1N citric acid (twice), water (twice), a saturated sodium bicarbonate solution then a saturated brine solution. After drying over magnesium sulfate, the solvent is removed under reduced pressure and the residue crystallized from chloroform/hexane. The solid is dried in vacuo at 40° giving 5.75 g of a solid, mp 136°-136.5° dec, [α]D23 -121.0° (c 2, methanol).

Provenance & Evidence