Sodium Methoxide → HCID 58928879, compound

Participants

Reaction Steps

A solution of 31 (5 mg, 0.01 mmol) in 0.3 mL of dry 0.5 M NaOMe was stirred at ambient temperature for 15 minutes when a yellow precipitate formed. The solvent was removed in vacuo and the solid was dissolved in a mixture of CH2Cl2— 1N HCl. The layers were separated and the aqueous layer was washed with CH2Cl2. The organic solvent was removed to provide an off-white solid. The product 32 was purified by trituration using CH2Cl2 and hexane. 1H NMR (300 MHz, CDCl3) δ 5.01 (s, 2H), 5.16 (s, 2H), 7.02 (dt, 2H, J=2, 9 Hz), 7.51 (ddd, 2H, J=2, 5, 9 Hz), 7.79 (dd, 1H, J=8, 5 Hz), 8.61 (dd, 1H, J=8, 2 Hz), 9.13 (dd, 1H, J=4, 2 Hz), 12.35 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 42.4, 46.1 107.0, 115.5, 115.8, 126.7, 127.1, 130.8, 131.4, 131.5, 132.5, 143.2, 148.4, 153.7, 156.0, 162.2 (d, J=249 Hz), 163.9, 164.0; EI MS (m/z) 354.6 [MH+].

Provenance & Evidence