Acetaldehyde → HCID 131728471, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (0.1 mL, 1.32 mmol) was added to a solution of Example 88k (0.28 g, 0.56 mmol) in methanol (15 mL) at 0° C. Acetaldehyde (2 mL) was added and stirring continued for 2 h. The reaction mixture was brought to room temperature, treated with sodium cyanoborohydride (0.203 g, 2.96 mmol) and allowed to stir overnight. It was then treated with an aqueous sodium bicarbonate solution and cooled to 0° C. The precipitated solid was filtered, washed with methanol, dried and purified using flash chromatography (silica gel, 0.5% methanol/chloroform) to obtain the title compound. Yield: 0.21 g, (67.5%); 1H NMR (CDCl3): δ 1.1 (m, 6H, 2CH3), 2.6 (m, 4H, 2CH2), 2.6 (s, 3H, CH3), 3.22 (t, 2H, CH2), 3.25 (t, 2H, CH2), 3.65 (s, 2H, CH2), 3.9 (s, 3H, OCH3), 4.53 (s, 2H, CH2), 6.22 (s, 1H, Ar), 6.52 (s, 1H, Ar), 7.35 (m, 5H, Ar), 8.1 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (ES+) 556 (M+1).

Provenance & Evidence