Ethyl 4-hydroxy-6-methyl-2-heptynoate → Ethyl 6-methyl-4-oxo-2-heptynoate

Participants

Reaction Steps

Jones' reagent (from chromium trioxide, 4 g) was added dropwise with stirring to ethyl 4-hydroxy-6-methyl-2-heptynoate (9.5 g) in acetone (30 ml) in an ice bath, with the temperature being maintained at about 10°. After 0.5 hour the reaction was diluted with water (300 ml) and extracted with diethyl ether thrice. The organic phase was washed with brine, dried, and evaporated to give ethyl 6-methyl-4-oxo-2-heptynoate as an oil (7.0 g).

Provenance & Evidence