Methanol → HCID 54271104, compound

Participants

Reaction Steps

(+/-)-1 -Phenyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-oxo-6-diazohexyne (120 mg, 0.35 mmol) was added portionwise to a refluxing solution of BF3 ·Et2O (0.5 ml) in MeOH (20 ml). After 5 min, the solvent was concentrated, the reaction diluted with H2O, basified with NaHCO3, and extracted with Et2O. The extracts were washed with H2O, dried, and the solvent removed. Purification by flash chromatography (silica gel, 30% Et2O in hexane) gave the titled product (4.8 mg, 4%). 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.30 (m, 3 H), 6.98 (m, 2 H), 6.84 (d, 1 H), 4.80 (m, 1 H), 4.40 (t, 1 H), 4.06 (d, 1 H), 3.92 (d, 1 H), 3.84 (s, 3 H), 3.38 (s, 3 H), 3.04 (d of d, 1 H), 2.88 (d of d, 1 H), 1.68-2.00 (m, 6 H), 1.58 (m, 2 H).

Provenance & Evidence