反应详情

温度

-20 °C

To a mixture of 10 g (0.059 mol) of 2,5-dimethoxybenzyl alcohol in 250 ml of ether cooled to -20° C. was added in portions 12.75 ml (0.127 mol) of n-butyllithium (10M) in hexane over a 10 min period, and the reaction mixture was allowed to warm to room temperature and stirred 1 hr. The above reaction mixture was cooled to -20° C., 7.58 g (0.07 mol) of pyridine-2-carboxaldehyde was added to the mixture, and the resulting reaction mixture was allowed to warm to room temperature (a brown precipitate formed) and stirred for 1 hr. Ammonium chloride solution (60 ml) was added, the mixture was extracted with ethyl acetate, the combined organic layer was washed with brine, dried over sodium sulfate, and concentrated. The diol was purified by chromatography on silica eluting with ethyl acetate/hexane (9:1) to afford 1.7 g (10.5%) of 2-[(2',5'-dimethoxy-6'-hydroxymethyl)benzyl]pyridine (Formula XIII: R1 =R7 =H; R2 =2',5'(OCH3)2), as a white solid, m.p. 102°-104° C.

1. temperatureto warm to room temperature
2. customThe above reaction mixture
3. temperaturewas cooled to -20° C.
4. customthe resulting reaction mixture
5. temperatureto warm to room temperature (a brown precipitate
6. customformed) and
7. stirringstirred for 1 hr
8. extractionthe mixture was extracted with ethyl acetate
9. washthe combined organic layer was washed with brine
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated
12. customThe diol was purified by chromatography on silica eluting with ethyl acetate/hexane (9:1)