Veratraldehyde → HCID 131728483, compound

Participants

Reaction Steps

Veratraldehyde (0.114 g, 0.687 mmol) and titanium isopropoxide (0.26 mL, 0.858 mmol) were added to a suspension of Example 104k (0.3 g, 0.687 mmol) in methanol (30 mL). The reaction mixture was refluxed for 1.5 h, cooled to room temperature, treated with sodium cyanoborohydride (0.042 g, 0.66 mmol) and stirred for 3 h. It was concentrated treated with water and extracted with 1-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 1% methanol/chloroform) to obtain the title compound. Yield: 0.335 g, (58.3%); 1H NMR (DMSO-d6): δ 2.65 (s, 3H, CH3), 3.2 (h, 4H, 2CH2), 3.4 (m, 4H, 2CH2), 3.5 (s, 2H, CH2), 3.75 (s, 6H, 20CH3), 3.9 (s, 3H, OCH3), 5.2 (s, 2H, CH2), 6.85-7.0 (m, 3H, Ar), 7.1 (s, 1H, Ar), 7.15 (d, 1H, Ar), 8.1 (s, 1H, Ar), 8.24 (s, 1H, Ar); MS: m/e (ES+) 588 (M+1).

Provenance & Evidence