Tetrahydrofuran → HCID 86757340, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 110 (13.3 mg, 24.4 μmol) in THF (0.3 mL) was treated with methyl (triphenylphosphoranylidene)acetate (23.9 mg, 71.5 μmol, 3 equiv). The reaction mixture was stirred for 48 h at 25° C. and the solvent removed under vacuum. Chromatography (SiO2, 10-25% EtOAc-hexane gradient elution) afforded 112 (9 mg, 14 mg theoretical, 63%) as an oil: 1H NMR (CDCl3, 400 MHz) δ 8.32 (d, J=8.2 Hz, 1H), 8.20 (d, J=8.2 Hz, 1H), 7.61-7.48 (m, 5H), 7.42-7.32 (m, 2H), 6.91 (m, 1H), 6.74 and 6.64 (two s, 1H), 5.79 (d, J=15.5 Hz, 1H), 5.31-5.23 (m, 2H), 3.81 (ddd, J=14.0, 9.6, 3.6 Hz, 1H), 3.70 (s, 3H), 3.35 (m, 1H), 2.18 (m, 2H), 1.75-1.55 (m, 2H), 1.29 and 1.24 (two s, 9H); IR (film) νmax 2975, 2947, 1702, 1658, 1471, 1391, 1366, 1307, 1272, 1162 cm−1.

Provenance & Evidence