反应详情

To a stirred room temperature solution of 3-fluoro-N-(4-hex-1-enyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide (2.7 g, 6.25 mmol) THF (15 ml) and water (5 ml) is added osmium tetroxide (2.5% in t-butanol) (100 μl) and sodium periodate (6 g) in portions over 30 minutes. After 1.5 hours, the mixture is diluted with ethyl acetate (200 ml) and washed with water (2×100 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by column chromatography on silica gel eluting with 25-30% ethyl acetate in hexanes to give 3-fluoro-N-(4-formyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide as a tan powder (1.072 g). Mp: 204-5° C. 1H NMR 400 MHz (CDCl3) δ 10.3 (s, 1H), 9.41 (d, 1H, J=8.8 Hz), 8.47 (d, 2H, J=7.6 Hz), 8.02 (d, 1H, J=8 Hz), 7.92 (d, 1H, J=8.4 Hz), 7.65-7.76 (m, 2H), 7.31 (s, 1H), 7.05 (d, 1H, J=8 Hz), 6.79 (d, 1H, J=11.6 Hz), 3.88 (t, 4H, J=5.2 Hz), 3.27 (t, 4H, J=5.2 Hz). MS: 379 (M+1).

1. washwashed with water (2×100 ml)
2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
3. customevaporated to dryness
4. customThe residue is purified by column chromatography on silica gel eluting with 25-30% ethyl acetate in hexanes