Ethyl Acetoacetate → Ethyl 5-(3-chlorophenyl)-3-oxopentanoate

Participants

Reaction Steps

Ethyl acetoacetate (78.6 g, 0.6 mole) was added to a slurry of sodium hydride (20.8 g of 75% dispersion in oil, 0.65 mole) in dry THF at 0° C. under nitrogen followed by addition of n-butyl lithium (390 ml, 1.6 M in hexane, 0.63 mole) by the method given in Description 1(a). 3-Chlorobenzyl chloride (100 g, 0.62 mole) was added and after work-up and purification by vacuum distillation the required product was obtained as a very pale yellowish green oil (97.3 g, 64%), δ(CDCl3) 7.3-6.9 (4H, m), 4.18 (2H, q, J=7 Hz), 3.42 (2H, s), 2.88 (4H, s), and 1.27 (3H, t, J=7 Hz).

Provenance & Evidence