Diethyl Ether → HCID 19373357, compound

Participants

Reaction Steps

n-Butyllithium (1.6 ml of a 1.1M solution in hexane) was added at -70° C. to a solution of 1-[4-(2,2-dibromovinyl)cyclohexyl]-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane (0.25 g) in dry tetrahydrofuran (5 ml) under a stream of nitrogen. After warming to room temperature over 2 hours ether (~25 ml) was added. The ethereal solution was washed with brine and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue was purified by column chromatography on alumina eluting with 3:7 dichloromethane:hexane saturated with ammonia. 1-(4-Ethynylcyclohexyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane was obtained as a colourless oil (0.13 g).

Provenance & Evidence