Ammonia → 7-Chloro-1-(2-furyl)-1-methoxy-3-heptyne

Participants

Reaction Steps

To a stirred mixture of 0.51 g of lithium amide and 25 ml of liquid ammonia was added a solution of 3.0 g of 4-(2-furyl)-4-methoxy-1-butyne in 2.5 ml of tetrahydrofuran. The mixture was stirred under reflux for 30 minutes and then treated with a solution of 3.94 g of 1-bromo-3-chloropropane in 5 ml of tetrahydrofuran. This mixture was stirred under reflux for one hour, then the ammonia was allowed to evaporate and the residue partitioned with ether and water. The ether layer was separated and evaporated. The residue was distilled at 0.06 mm on a Kugelrohr, giving 3.07 g of the desired compound as an oil, bp 110°-120° C.

Provenance & Evidence