Hydrochloric Acid → Methyl 3-oxo-6-heptenoate

Participants

Reaction Steps

Methyl acetoacetate (34.8 g) is added dropwise to a suspension of 16.2 g of 50% sodium hydride in 750 mL of anhydrous tetrahydrofuran cooled to 0°. To this solution is added dropwise 141 mL of a 2.3M solution of n-butyllithium in hexane over 40 minutes keeping the temperature of the THF solution at 0°. To this solution is then added 36 g of a solution of allyl bromide in 150 mL of THF. After 10 minutes the reaction is worked up by pouring into a mixture of 60 mL of aqueous concentrated HCl, 150 mL of water and 500 mL of ether. The ether layer is separated, washed with water, dried over magnesium sulphate, filtered and evaporated to give methyl 3-oxo-hept-6-enoate.

Provenance & Evidence