反应详情

温度

90 °C

A magnetically stirred suspension of sodium cyanide (13.65 g, 265 mmol) in anhydrous methyl sulfoxide (65 mL) was treated dropwise with 3-(3-methoxyphenyl)propyl iodide (66.25 g, 240 mmol) at a rate sufficient to keep the temperature below 45° C. The suspension was heated at 90° C. for 1 h, cooled to room temperature, poured over ice (1000 g), treated with diethyl ether (500 mL), the layers separated, and the aqueous portion back-extracted with diethyl ether (2×300 mL). The combined organic extracts were washed with water (3×500 mL), 6N HCl (500 mL), brine (500 mL), dried (MgSO4), filtered, and concentrated in vacuo to a clear liquid. Kugelrohr distillation (0.1 torr, 120° C.) provided the desired product as a clear liquid (37.62 g, 89%): 1H NMR (CDCl3) δ 7.25 (t, J=8 Hz, 1H), 6.78-6.69 (m, 3H), 3.80 (s, 3H), 2.75 (t, J=8 Hz, 2H), 2.31 (t, J=8 Hz, 2H), 1.98 (quint, J=8 Hz, 2H).

1. customthe temperature below 45° C
2. temperaturecooled to room temperature
3. customthe layers separated
4. extractionthe aqueous portion back-extracted with diethyl ether (2×300 mL)
5. washThe combined organic extracts were washed with water (3×500 mL), 6N HCl (500 mL), brine (500 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo to a clear liquid
9. distillationKugelrohr distillation (0.1 torr, 120° C.)