Allyltrimethylsilane → HCID 58237930, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5-chloro-3-hydroxy-3-phenylpentanoate (1.0 g, 3.9 mmol) in anhydrous CH2Cl2 (20 mL) cooled to −78° C. under nitrogen was added allyltrimethylsilane (4.5 g, 39 mmol) followed by a solution of TiCl4 in CH2Cl2 (16 mL, 1 mol/L) dropwise. The solution was stirred at −78° C. for 30 min, and then was heated to reflux overnight. The reaction was quenched with aqueous Na2CO3 solution. The organic phase was separated and concentrated to give the crude product, which was purified by column chromatography to afford the ethyl 3-(2-chloroethyl)-3-phenylhex-5-enoate (0.5 g, 45%). 1H NMR (CDCl3): δ=1.08 (t, 3H), 2.24 (m, 2H), 2.54 (m, 2H), 2.68 (d, 2H), 3.19 (m, 1H), 3.26 (m, 1H), 3.96 (q, 2H), 5.01 (m, 2H), 5.51 (m, 1H), 7.14 (m, 1H), 7.19 (m, 2H), 7.29 (m, 2H).

Provenance & Evidence