Water → 3-fluoro-N-(4-formyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide

Participants

Reaction Steps

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).

Provenance & Evidence