3-Ethoxycyclohept-2-en-1-one → 3-Phenethylcycloheptenone

Participants

Reaction Steps

3-Ethoxycycloheptenone was synthesized following published procedures.8 The general procedure for the preparation of substrates using 3-ethoxycycloheptenone (766 mg, 4.97 mmol) and phenethymagnesium chloride (10 mmol, 1M in THF) gave, after flash chromatography (4:1 hexanes:ethyl acetate), the title compound as a colorless liquid (0.984 g, 93%). 1H NMR (300 MHz, CDCl3): δ7.32-7.13 (m, 5 H), 5.91 (br s, 1 H), 2.79 (dd, J=10.5, 7.8 Hz, 2 H), 2.64-2.39 (m, 6 H), 1.86-1.70 (m, 4 H). 13C NMR (75 MHz, CDCl3): δ204.0, 161.1, 140.9, 129.6, 128.5, 128.3, 126.3, 43.0, 42.4, 34.4, 33.1, 25.4, 21.5. IR (neat): 3027, 2937, 2865, 1656, 1495, 1453, 1268, 878, 747, 699 cm−1.

Provenance & Evidence