Lithium Chloride → Ethyl (1-vinylcyclopropyl)acetate

Participants

Reaction Conditions

Reaction Steps

Under argon, 0.55 g (5.53 mmol) of copper(I) chloride and 0.59 g (13.82 mmol) of lithium chloride are suspended in 150 ml of anhydrous THF. The reaction mixture is cooled to −78° C., 48.8 ml (82.95 mmol) of vinylmagnesium chloride solution (1.7 M in THF) are added and the mixture is stirred for 10 minutes. Over a period of 30 min, a solution of 8.72 g (69.12 mmol) of ethyl cyclopropylideneacetate (Example 1A) in 50 ml of anhydrous THF is then added dropwise. After the addition is ended, the cooling bath is replaced by an ice/acetone bath. After a further 15 min, the reaction is terminated by dropwise addition of 100 ml of 1 N hydrochloric acid. The reaction mixture is saturated with sodium chloride, and 100 ml of a saturated sodium chloride solution which contains 5 ml of a 25% strength aqueous ammonia solution are then added. The mixture is filtered through Celite. The filtrate is washed with ammoniacal sodium chloride solution until the aqueous phase remains colorless. The organic phase is washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent and kugelrohr distillation of the residue at 150° C. and 15 mbar gives 7.10 g (67% of theory) of the title compound as a colorless liquid.

Provenance & Evidence