Benzaldehyde → HCID 131728519, compound

Participants

Reaction Steps

Sodium acetate (0.107 g, 1.30 mmol) was added to a solution of Example 198k (0.2 g, 0.52 mmol) in dry methanol (15 mL). Subsequently benzaldehyde (0.083 mL, 0.78 mmol) was added and the reaction mixture was stirred for 2.5 h. It was then chilled and treated with sodium borohydride (0.19 g, 0.52 mmol). The reaction mixture was stirred overnight at room temperature, then treated with an aqueous 10% sodium bicarbonate solution (2 mL), diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.095 g, (38.46%); 1H NMR (DMSO-d6): δ 2.70 (s, 3H, CH3), 3.81 (s, 4H, 2CH2), 3.91 (s, 3H, OCH3), 4.71 (s, 2H, CH2), 7.26-7.34 (m, 5H, Ar), 7.51 (s, 1H, Ar), 8.09 (s, 2H, Ar), 8.46 (s, 1H, Ar); MS: m/e (EI+) 472 (M+1).

Provenance & Evidence