Acetaldehyde → HCID 131728469, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (0.05 mL, 0.67 mmol) was added to a solution of Example 86k (0.17 g, 0.335 mmol) in methanol (10 mL) at 0° C. Acetaldehyde (1 mL, 19.5 mmol) was added and the reaction mixture was stirred at 0-10° C. for 2 h. The reaction mixture was brought to room temperature, treated with sodium cyanoborohydride (0.092 g, 1.34 mmol) and left stirring overnight. It was treated with an aqueous sodium bicarbonate solution, concentrated, treated with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 20% ethyl acetate/pet ether) to obtain the title compound. Yield: 0.11 g, (58.3%); 1H NMR (CDCl3): δ 1.1 (q, 6H, 2CH3), 2.62 (t, 4H, 2CH2), 2.65 (s, 3H, CH3), 3.32 (m, 4H, 2CH2), 3.83 (s, 2H, CH2), 3.92 (s, 3H, CH3), 5.2 (s, 2H, CH2), 6.32 (s, 1H, CH2), 6.52 (s, 1H, Ar), 7.00 (m, 2H, Ar), 7.32 (s, 1H, Ar), 8.1 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (ES+) 563 (M+1).

Provenance & Evidence