P-Chloroacetophenone → HCID 360612, compound

Participants

Reaction Steps

To a solution of lithium isopropylcyclohexylamide (prepared from 12.5 ml of n-butyllithium 1.6M solution and isopropyl cyclohexylamine (3.3 ml) (ex Aldrich) in TMF was added at -60°, ethyltrimethylsilylacetate (3.6 ml) (ex Fluka). After 30 minutes at -60°, 4-chloro acetophenone (ex Aldrich) (1.55 g) was added. After 18 hours at 25° the mixture was partitioned between ether and water and worked up in the usual manner. Purification by chromatography (silica; ether/hexane) gave Ethyl-3-(4-chlorophenyl)-but-2-enoate (1.22 g), as a 1:1 mixture of E:Z olefin isomers. NMR 1H: 7.2(4H,m), 6.0 and 5.0(1H,m), 4.12(2H,m), 2.51 and 1.90(3H,s), 1.25(3H,m).

Provenance & Evidence