Dimethyl Sulfoxide → HCID 22610231, compound

Participants

Reaction Conditions

Reaction Steps

2 ml of oxalyl chloride were dissolved in 100 ml of methylene chloride and treated at −70° C. dropwise with 2.8 g of dimethylsulfoxide. The reaction mixture was warmed for 5 minutes to −35° C., cooled again to −60° C. and treated dropwise with a solution of 2.9 g of (4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-inden-2-yl)-methanol in 20 ml of methylene chloride. After 15 minutes of stirring at −50° C., 5 ml of triethylamine were added dropwise. The reaction mixture was stirred at room temperature for 3 hours, then poured onto ice/water, extracted with methylene chloride, dried (Na2SO4) and the solvent was evaporated. The yellow, oily residue was purified with flash chromatography (silica gel, hexane/ethyl acetate=20:1) to yield 2.8 g of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carbaldehyde as colorless oil.

Provenance & Evidence