Sodium Azide → HCID 18538111, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium azide (2.12 g, 32.6 mmol) in dimethylformamide (15 mL) cooled to 0° C. was added dropwise with stirring 4-bromocyclopent-2-enone (DePuy, C. H.; Isaks, M.; Eilers, K. L.; Morris, G. F. J. Org. Chem. 1964. 29, 3503; 3.5 g, 21.7 mmol) in dimethyl-formamide (5 mL) over a period of 5 min. The reaction mixture was stirred at 0° C. for 30 min and diluted with ethyl acetate (20 mL). The reaction mixture was washed with water (2×20 mL) and brine (20 mL), dried (MgSO4), filtered, and concentrated in vacuo to furnish an oily residue. Purification of the crude oil by flash column chromatography (10-15% ethyl acetate in hexane) gave 1.9 g (71%) of 4-azidocyclopent-2-enone as a light-yellow oil.

Provenance & Evidence