Acetaldehyde → HCID 67668838, compound

Participants

Reaction Steps

A solution of 1,1 -dibromo-2-{cis-3-(4-fluorophenoxy)cyclopentyl}ethene (6.12 g, 18 mmol) in dry THF (50 ml) at -78° C. under an argon atmosphere was added n-butyllithium (24.5 ml, 39 mmol, 1.6M n-hexane solution). The mixture was stirred for 0.5 h at the same temperature and then allowed to warm to room temperature over 1 h. The mixture was cooled to 0° C., a solution of dry acetaldehyde (1.76 g, 40 mmol) in dry THF (20 ml) added to the mixture and the whole stirred overnight at room temperature. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (100 ml) and the whole extracted with ethyl acetate (200 ml). The combined extracts were washed with brine (200 ml), dried (MgSO4) and concentrated in vacuo. Purification by column chromatography {SiO2, 250 g; hexane/ethyl acetate (4:1)} afforded 2.18 g (49%) of title compound as a yellow oil: 1H NMR δ7.05-6.92 (m, 2H), 6.86-6.77 (m, 2H), 4.78-4.62 (m, 1H), 4.60-4.48 (m, 1H), 2.81-2.65 (m, 1H), 2.52-2.36 (m, 1H), 2.12-1.81 (m, 5H), 1.65 (br.s, 1H), 1.45-1.40 (m, 3H).

Provenance & Evidence