Triethylamine → 2-[3-(Benzenesulfonyl)-1,1,1-trifluoropropan-2-yl]-2-methyloxirane

Participants

Reaction Steps

Under an argon atmosphere, 1.45 ml (18.7 mmoles) of methanesulfonyl chloride was added under ice cooling to a solution of 3.90 g (12.5 mmoles) of the compound (18) and 6.10 ml (43.8 mmoles) of triethylamine in 25 ml of methylene chloride, and the mixture was stirred for 3.5 hours while the temperature was being returned to room temperature. To the reaction mixture was added 5.60 ml (37.4 mmoles) of 1,8-diazabicyclo[5,4,0]-7-undecene, and the mixture was stirred for 2.5 hours. The reaction mixture was poured into ice-dilute hydrochloric acid, and extracted with ether. The ether extract was washed with saturated aqueous sodium bicarbonate solution and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (150 g; n-hexane:ethyl acetate=5:1 to 3:1 v/v) to give 3.02 g of the captioned compound (19) as a colorless oil.

Provenance & Evidence