Hydrochloric Acid → 5-(3-Ethylphenyl)-3-oxopentanoic acid, ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl acetoacetate (25 g) in tetrahydrofuran (800 ml) at 0° C. was added LDA (2.0M solution in heptanes/tetrahydrofuran/ethylbenzene) (194 ml). After 40 min the product from step (ii) (39 g) was added dropwise and the mixture was stirred at 0° C. for 1 hour. The reaction mixture was acidified with 2N HCl and the organic phase was concentrated under reduced pressure. The residue was dissolved in diethyl ether and washed with water and saturated brine. The organic phase was collected, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 5-10% ethyl acetate in isohexane.

Provenance & Evidence