Ammonia → HCID 70021403, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the arene 1 (1.63 g, 5 mmol) in THF (25 mL) was condensed liquid ammonia (100 mL). Small pieces of freshly cut lithium wire (0.6 g, 86 mmol) were added over a period of 5 min at −50° C. The deep blue solution was stirred at −33° C. for 30 min and ethanol (100%, 10 mL) was added over a period of 10 min. The ammonia was allowed to evaporate and water (20 mL) was added. The biphasic mixture was transferred to a separatory funnel and extracted with ether (3×30 mL). The ether extracts were combined, washed with brine, dried over potassium carbonate and concentrated to afford a shiny white solid which was washed with ether (4×20 mL) to give the enol ether 2 (1.2 g, 73%).

Provenance & Evidence