Methyl iodide → HCID 54386275, compound

Participants

Reaction Steps

A solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-phenylpent-4-ynol (175 mg, 0.5 mmol) in a mixture of glyme (7 ml) and DMF (2 ml) was treated with NaH (20 mg of a 60% dispersion in mineral oil), heated to 50° for 3 min, and cooled to 23°. MeI (0.5 ml) was added, and the mixture stirred for 18 hr. Me2SO4 (0.3 ml) was added, and the mixture was heated to 60° for 2 hr. The reaction was cooled, quenched with 50 ml cold 0.1N HCl, and extracted with Et2O. The extracts were washed with H2O, dried, and the solvent evaporated. Purification by flash chromatography (silica gel, 30% EtOAc in hexane) gave the titled compound, (26 mg 14%). 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.28 (m, 3 H), 6.96 (m, 2 H), 6.82 (d, 1 H), 4.80 (m, 1 H), 3.98 (t, 1 H), 3.84 (s, 3 H), 3.62 (m, 1 H), 3.48 (m, 1 H), 3.40 (s, 3 H), 2.06 (m, 2 H), 1.72-2.00 (m, 6 H), 1.62 (m, 2 H).

Provenance & Evidence