Water → HCID 21217975, compound

Participants

Reaction Steps

Part A. A mixture of 3-cyanobenzaldehyde (2.0 gm, 15.2 mmol), 1-ethoxy-1-trimethylsilyloxycyclopropane (3.44 gm, 19.73 mmol) and zinc iodide (0.12 gm, 0.38 mmol) in 30 mLs methylene chloride under a nitrogen atmosphere was stirred at ambient temperature for 18 hrs. The reaction mixture was poured into water and extracted with methylene chloride. The combined organic layers was washed with water, brine, dried over magnesium sulfate and concentrated to give the crude product as a yellow oil. The oil was purified by flash chromatography on silica gel (100 mLs) eluting hexane:ethyl acetate (v:v, 90:10) to give ethyl 3-(cyano)-gamma-(trimethylsilyloxy)benzenebutanoate as a viscous oil 1.75 gm (38% yield) MS 323(M+H)+, 1H NMR (CDCl3) 7.8(s, 1H), 7.5(d, 2H), 7.39(t, 1H), 4.73(m, 1H), 4.07(q, 2H), 2.41-2.2 (m, 2H), 2.0-1.8(m, 2H), 1.20(t, 3H), 0.03 (s, 9H).

Provenance & Evidence