Tetrabutylammonium Fluoride → 1-(Hex-5-ynyl)-4-n-propyl-2,6-dioxabicyclo[2.2.2]octane

Participants

Reaction Steps

Tetrabutylammonium fluoride solution (1.0M.,solution 4.0 ml.) was added to a stirred solution of 4-n-propyl-1-(6-trimethylsilylhex-5-ynyl)-2,6-dioxabicyclo[2.2.2]octane in dry tetrahydrofuran (40 ml.) at 20° and the mixture was stirred for 1 hour. The solvent was removed in vacuo and the residue was extracted with diethyl ether and water. The ethereal extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was chromatographed on alumina eluting with dichloromethane: hexane 1:9, saturated with ammonia. 1-(Hex-5-ynyl)-4-n-propyl-2,6-dioxabicyclo[2.2.2]octane was obtained as a colourless oil (0.45 g.)

Provenance & Evidence