Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 67740254, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[2-(2-ethoxy-4-formylphenyl)ethynyl]quinuclidin-3-ol (598 mg), carbethoxymethylenetriphenylphosphorane (1.04 g) in toluene (10 ml) was heated at 100° C. for 5 hours. The reaction mixture was cooled to ambient temperature and the toluene evaporated to give a solid which was crystallised from acetonitrile to give 3-[2-(2-ethoxy-4-(2-ethoxycarbonylethenyl)phenyl)ethynyl]quinuclidin-3-ol (328 mg) as a solid, m.p. 152-153° C.; microanalysis found: C, 71.5; H, 7.3; N, 3.7%; C22H27NO4 requires: C, 71.5: H, 7.37; N, 3.79%; NMR (CDCl3): 1.33(3H, t), 1.36-1.52(4H, m), 1.55-1.70(1H, m), 1.90-2.30(4H, m), 2.73-3.00(4H, m), 3.04(1H, d), 3.34(1H, dd), 4.09(2H, q), 4.26(2H, q), 6.33-6.45(1H, d), 6.93-7.03(1H, d,), 7.03(1H, dd), 7.35(1H, d), 7.60(1H, d); m/Z 370 (M+H).

Provenance & Evidence