Methyl formate → 2-Butyl-3-dimethylaminosulfonylim idazole4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

1.25 g of 2-butyl-3-dimethylaminosulfonylimidazole was dissolved in 25 ml of tetrahydrofuran and cooled to -70° C., and 3.3 ml of n-butyllithium, 1.6 n in hexane, was added. After 1 hour, 0.64 ml of methyl formate was added, and the mixture was heated to room temperature and stirred for 17 hours at this temperature. The mixture was then concentrated, methylene chloride/water was added and the mixture was neutralized by adding 10 percent strength sulfuric acid. The organic phase was dried with Na2SO4 and concentrated by evaporation to give 1.35 g of crude product in the form of a yellow oil, which was purified by chromatography over methylene chloride/methanol/hexane 90:5:5 to give 0.99 g of product. The yield was 76 percent. Other data concerning the roduct was:

Provenance & Evidence