反应详情

温度

10 °C

Pentanaldehyde (0.042 gm, 0.5 mmol) was added with stirring to a solution of Example 104k (0.180 g, 0.4 mmol) in dry methanol (10 mL). Titanium isopropoxide (0.117 g, 0.4 mmol) was added and the reaction mixture was cooled to 10° C. Sodium cyanoborohydride (51 mg, 0.8 mmol) was added and the reaction mixture was heated at 60° C. overnight. 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, 1-3% MeOH/CHCl3) to obtain the title compound. Yield: 0.2 g (99%), 1H NMR (CDCl3): δ 0.90 (s, 3H, CH3), 1.3 (t, 4H, 2CH2), 1.7 (t, 2H, CH2), 2.40 (t, 2H, CH2), 2.8 (t, 4H, 2CH2), 2.90 (s, 3H, CH3), 3.20 (t, 4H, 2CH2), 3.90 (s, 3H, CH3), 4.8 (s, 2H, CH2), 6.70 (s, 1H, Ar), 6.90 (s, 1H, Ar). 8.1 (s 1H Ar), 8.4 (s 1H Ar); MS: m/e (EI+) 507 (M+1).

1. temperaturethe reaction mixture was heated at 60° C. overnight
2. concentrationIt was concentrated
3. additiontreated with water
4. extractionextracted with n-butanol
5. washThe organic layer was washed with water, brine
6. concentrationconcentrated
7. custompurified