Citric Acid → Isohexane ethyl acetate

Participants

Reaction Steps

A mixture of (syn)-5-chloro-N-(2-oxobicyclo[2.2.1]hept-7-yl)thiophene-2-sulfonamide (0.100 g, 0.313 mmol), methyl(triphenylphosphonium) bromide (0.125 g, 0.35 mmol) and potassium tert-butoxide (1M in THF, 1.0 mL) in dry toluene (2 mL) was reluxed under N2 for 4 h. The mixture was cooled, diluted with 1M citric acid (15 mL) and extracted with EtOAc (2×15 mL). The extracts were dried (Na2SO4), filtered and concentrated. Flash column chromatography, eluting with 10% then 20% EtOAc-isohexane, gave the title compound as a pale yellow solid (0.027 g, 28%). 1H NMR (CDCl3, 360 MHz) δ 1.30-1.34 (2 H, m), 1.69-1.73 (2 H, m), 1.96 (1 H, d, J 15), 2.26-2.35 (2 H, m), 2.41 (1 H, d, J 3), 3.42 (1 H, d, J 6), 4.55 (1 H, d, J 6), 4.83 (1 H, s), 4.95 (1 H, s), 6.92 (1 H, d, J 4), 7.39 (1 H, d, J 4); m/z 306 and 304 (M+H+).

Provenance & Evidence