反应详情

A 1M solution of sodium methoxide in methanol (1.1 mL) was added to a solution of 322 (3.10 g, 4.13 mmol) in methanol. The mixture was stirred at rt for 3 h. The mixture was neutralised with Amberlite IR-120 (H+) resin, filtered and concentrated to give 323 (2.72 g, 93%) as a colourless syrup which crystallised on standing; mp 98-99° C.; lit. (Pinto, B. M.; Reimer, K. B.; Morissette, D. G.; Bundle, D. R. J. Org. Chem. 1989, 54, 2650-2656) mp 100° C. (hexane); [α]D−30° (c 0.5, CHCl3), lit. (Pinto, B. M.; Reimer, K. B.; Morissette, D. G.; Bundle, D. R. J. Org. Chem. 1989, 54, 2650-2656) [α]D−32.5° (c, 0.4, CHCl3); 1H NMR: δ 7.42-7.30 (m, 20H, Ph), 5.90-5.80 (m, 1H, All), 5.32-5.20 (m, 2H, All), 5.13 (d, 1H, J1,2=1.4 Hz, H-1A), 4.82 (d, 1H, J1,2=1.6 Hz, H-1B), 4.95-4.60 (m, 8H, CH2Ph), 4.20-4.12 (m, 1H, All), 4.19 (m, 1H, J2,3=3.2, J2,OH=1.8 Hz, H-2A),4.09 (d, 1H, J2,3=3.2 Hz, H-2B), 4.00-3.95 (m, 1H, All), 3.95 (dd, 1H, J3,4=9.4 Hz, H-3A), 3.93 (dd, 1H, J3,4=9.4 Hz, H-3B), 3.87 (dq, 1H, J4,5=9.4, J5,6=6.2 Hz, H-5A), 3.74 (dq, 1H, J4,5=9.4, J5,6=6.2 Hz, H-5B), 3.53 (pt, 1H, H-4A), 3.46 (pt, 1H, H-4B), 2.52 (d, 1H, OH), 1.35 (m, 6H, H-6A, 6B); 13C NMR: δ 138.4-117.1 (Ph, All), 101.2 (C-1A), 98.4 (C-1B), 80.8, 80.4 (2C, C-4A, 4B), 80.3 (C-3B), 80.0 (C-3A), 75.8, 75.7 (2C, CH2Ph), 75.0 (C-2B), 72.7, 72.6 (2C, CH2Ph), 69.1 (C-2A), 68.4 (C-5B), 68.3 (C-5A), 68.1 (All), 18.4, 18.3 (2C, C-6A, 6B). CI-MS for C43H50O9 (M, 710) m/z 728 [M+NH4]+.

1. filtrationfiltered
2. concentrationconcentrated