Decanal → 4-Chloro-2-(4-decyl-piperazin-1-yl)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Decanaldehyde (0.071 g, 0.45 mmol) was added with stirring to a solution of Example 104k (0.2 g, 0.45 mmol) in dry methanol (5 mL). Titanium isopropoxide (0.12 g, 0.45 mmol) was added and the reaction mixture was cooled to 10° C. Sodium cyanoborohydride (0.057 g, 0.9 mmol) was added and the reaction mixture was refluxed for 2 h. It was concentrated, treated with water and extracted with n-butanol. The organic layer was washed with water, brine, concentrated and purified using flash chromatography (silica gel, MeOH/CHCl3) to obtain the title compound. Yield: 0.120 g (46%); 1H NMR (CDCl3): δ 0.90 (s, 5H, CH3CH2), 1.20 (m, 12H, 6CH2), 2.28 (s, 4H, 2CH2), 2.30 (t, 2H, CH2), 2.70 (t, 3H, CH3), 3.20 (t, 4H, 2CH2), 3.90 (s, 3H, OCH3), 4.80 (s, 2H, CH2), 6.80 (s, 1H, Ar), 7.00 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.4 (s 1H Ar); MS: M/e (EI+) 577 (M+1).

Provenance & Evidence