N-methoxy-N-methylisoxazole-3-carboxamide → 1-(3-Isoxazolyl)-2-propen-1-one

Participants

Reaction Conditions

Reaction Steps

The product of step (a) (0.66 g) was dissolved in dry tetrahydrofuran (20 ml), under a nitrogen atmosphere and cooled to −30° C. A solution of vinyl magnesium bromide (1M, 6 ml) was added dropwise over 5 minutes and the reaction mixture was allowed to warm to 0° C. and stirred at this temperature for 2 h. The mixture was then poured into ice-cold 2N hydrochloric acid (50 ml) and extracted into ethyl acetate. The extract was washed with water, brine, dried over magnesium sulphate and evaporated to give a dark oil (0.4 g).

Provenance & Evidence