HCID 59280012, compound → HCID 46205077, compound

Participants

Reaction Steps

To a solution of dichloro compound 2h (1.00 g, 3.66 mmol) in dry ethanol (100 mL), under argon, was added 4-dimethylaminopyridine (DMAP) (0.90 g, 7.38 mmol). The solution was stirred under reflux for 20 h. After cooling to room temperature, the solution was concentrated under vacuo. The resulting precipitate was suspended in ethyl acetate (30 mL), filtered and washed with AcOEt (3×10 mL). The filtrate was evaporated to dryness. The crude product was chromatographed using AcOEt/cyclohexane (8/2, v/v) as eluent to afford compound 2i (1.04 g, 97%). Ketal compound 2i (0.30 g, 4%); mp 98-100° C.; IR (KBr) 1716, 1267, 1166 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.24 (t, 6H, J=7 Hz), 1.41 (t, 3H, J=7 Hz), 3.68 (m, 4H), 4.46 (q, 2H, J=7 Hz), 5.81 (s, 1H), 6.85 (t, 1H, J=7 Hz), 7.78 (s, 1H), 7.90 (d, 1H, J=7 Hz), 8.32 (d, 1H, J=7 Hz); 13C NMR (100 MHz, CDCl3) δ 14.3, 15.3, 61.6, 62.3, 99.0, 111.0, 111.5, 120.2, 128.9, 129.8, 142.0, 146.3, 164.2. MS m/z 293 (M++1, 1), 248 (22), 219 (100), 191 (17), 173 (52), 146 (18) 117 (13).

Provenance & Evidence