反应详情

温度

-20 °C

To a mixture of 30 g (0.18 mol) of 3-isopropoxybenzyl alcohol in 600 ml of ether cooled to -20° C. was added in portions 38.7 ml (0.387 mol) of n-butyllithium (10M) in hexane over a 20 min period, and the reaction mixture was allowed to warm to room temperature and stirred for 2 hr. The above reaction mixture was cooled to -20° C., 23.1 g (0.216 mol) of pyridine-2-carboxaldehyde was added in one portion to the mixture, and the resulting reaction mixture was allowed to warm to room temperature and stirred for 1 hr. Ammonium chloride solution (200 ml) and 100 ml of ethyl acetate were added to the mixture. The resulting mixture was separated, the aqueous layer was extracted with methylene chloride (2×200 ml), the combined organic layer was washed with brine, dried over sodium sulfate, and concentrated. The diol was purified by chromatography on silica gel eluting with ethyl acetate/hexane (9:1; and 0.05 % TEA). The solvent was concentrated in vacuo, the brown oil was dissolved in methylene chloride/hexane, and removal of methylene chloride in vacuo to 1/2 of its volume afforded 11.1 g (22.6%) of 2-[1-hydroxy-(6'-hydroxymethyl-2'-isopropoxy) -benzyl]pyridine (Formula XIII: R1 =R7 =H; R2 =2'--OCH (CH3)2), as a tan solid.

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
6. stirringstirred for 1 hr
7. customThe resulting mixture was separated
8. extractionthe aqueous layer was extracted with methylene chloride (2×200 ml)
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 gel eluting with ethyl acetate/hexane (9:1; and 0.05 % TEA)
13. concentrationThe solvent was concentrated in vacuo
14. dissolutionthe brown oil was dissolved in methylene chloride/hexane
15. customremoval of methylene chloride in vacuo to 1/2 of its volume