Sodium Methoxide → HCID 58928994, compound

Participants

Reaction Steps

To a solution of 36 (0.900 g, 2.26 mmol) in 12 mL of dry MeOH under a N2 atmosphere was added 12.5 mL of a 0.5 M sodium methoxide (NaOMe). The solution was stirred at ambient temperature for 2.5 hours. The reaction was worked up by removing the solvent and dissolving the residue in CH2Cl2. The organic layer was washed with a saturated aqueous solution of NH4Cl and dried to provide 610 mg of the product 37 as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 3.58 (t, 2H, J=6 Hz), 4.308 (t, 2H, J=5 Hz), 4.77 (s, 2H), 7.09 (t, 2H, J=8 Hz), 7.34 (t, 2H, J=8 Hz), 7.61 (dd, 1H, J=5.8 Hz), 8.73 (d, 1H, J=8 Hz), 9.12 (d, 1H, J=3 Hz), 13.00 (s, 1H); 13C NMR (75 M, CDCl3) δ 38.8, 43.9, 49.5, 111.9, 115.9, 116.2, 124.7, 130.0, 130.1, 131.0, 136.4, 146.8, 147.2, 154.7, 157.3, 163.0 (d, J=245 Hz), 163.7; 19F NMR (282.6 MHz, CDCl3) δ 63.2; EI MS (m/z) 340.5 [MH+], 362.3 [M+Na].

Provenance & Evidence