Acetaldehyde → HCID 131728467, compound

Participants

Reaction Steps

Trifluoroacetic acid (0.03 mL, 0.4 mmol) was added to mixture of Example 84k (0.2 g, 0.40 mmol) and acetaldehyde (0.115 mL, 2 mmol) in dry methanol (10 mL) at 0° C. The reaction mixture was stirred at room temperature in an atmosphere of nitrogen for 1.5 h. It was treated with sodium cyanoborohydride (0.064 g, 1 mmol), stirred for 1.5 h, treated with cold water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried and purified using flash chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound as a white solid. Yield: 0.285 g, (68.69%); 1H NMR (DMSO-d6): δ 1.1 (t, 6H, 2CH3), 2.60-2.69 (m, 4H, 2CH2), 2.70 (s, 3H, CH3), 3.30-3.40 (m, 4H, 2CH2), 3.70 (s, 2H, CH2), 3.95 (s, 3H, OCH3), 4.65 (s, 2H, CH2), 6.25-6.85 (m, 3H, Ar), 6.65 (s, 1H, Ar), 7.45 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.50 (s, 1H, Ar); MS: m/e (CI+) 547 (M+1).

Provenance & Evidence