Water → HCID 52951813, compound

Participants

Reaction Steps

To a solution of compound 42 (6.50 g, 46.1 mmol) in anhydrous ethyl acetate (250 mL) were added successively at 0° C., under argon, triethylamine (6.40 mL, 46.0 mmol) and dropwise methanesulfonyl chloride (3.60 mL, 46.5 mmol). The mixture was stirred at 0° C. for 10 min before addition of water (200 mL) at room temperature. The mixture was extracted with ethyl acetate (3×200 mL). The organic layers were combined, dried on magnesium sulfate, filtered and evaporated under vacuum. The residue was chromatographed (Al2O3, CH2Cl2) to give sulfonate 43 (7.56 g, 34.5 mmol) as a yellow oil. Yield 75%; Rf (Al2O3, CH2Cl2) 0.52; IR (CCl4) ν 1179, 1352, 1414, 1613 cm−1; 1H NMR (200 MHz, CDCl3) δ 2.95 (s, 3H), 3.09 (t, 2H, J=6.4 Hz), 4.45 (t, 2H, J=6.4 Hz), 6.82 (s, 1H), 7.07 (d, 1H, J=5.1 Hz), 8.15 (d, 1H, J=5.1 Hz); MS m/z 219 (M+, 3), 123 (100), 111 (30), 83 (14), 79 (53), 57 (11).

Provenance & Evidence