Sodium borohydride → 1-[2-(6-Methoxy-naphthalen-2-yl)-benzofuran-3-yl]-pentan-1-ol

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Reaction Steps

Sodium borohydride ((7.56 g, 200 mmol) was added portion-wise to the stirring mixture of 1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (17.9 g, 50 mmol) in ethanol (600 mL). The mixture was stirred at room temperature for 2 hours then filtered. The solids were dissolved in methylene chloride and 2N hydrochloric acid solution. The organic phase was washed with water, dried over anhydrous magnesium sulfate and solvent evaporated to give the title compound (16.6 g). 1HNMR (300 MHz, DMSO-d6): δ8.2 (s, 1H), 7.98-7.92 (m, 2H), 7.9-7.82 (m, 2H) 7.62 (d, 1H, J=7.5 Hz), 7.38 (s, 1H), 7.35-7.22 (m, 3H), 5.46 (d, 1H, J=3.6 Hz), 5.15-5.07 (m, 1H), 3.92 (s, 3H), 2.12-1.97 (m, 1H), 1.95-1.82 (m, 1H), 1.44-1.21 (m, 3H), and 0.69 ppm (t, 3H, J=7.4 Hz).

Provenance & Evidence