反应详情

Under a nitrogen atmosphere, alpha-(4-picolylthio)p-methoxyacetophenone (1.99 g., 7.3 mmoles) was dissolved in 25 ml. of stirring ethanol. Sodium borohydride (0.45 g., 11.7 mmoles) was added portionwise and the mixture then refluxed gently for 30 minutes. The mixture was partially cooled and evaporated to dryness. Water (50 ml.) was added to the residue, which was then acidified with excess 1N hydrochloric acid. The acid solution was made basic with solid sodium bicarbonate and product extracted into ethyl acetate. The ethyl acetate was dried over anhydrous sodium sulfate and concentrated to an oil, which crystallized on standing. Trituration with diethyl ether and filtration gave purified 4-[2-(4-methoxyphenyl)-2-hydroxyethylthiomethyl]pyridine (1.50 g.; m.p. 70°-72.5° C.; pnmr/CDCl3 /TMS/delta: 7.2 (d, 2H), 6.4 (s, 2H), 6.3 (1H, exchanges with D2O), 6.2 (d, 3H), 5.3 (t, 1H), 3.2 (broad doublet, 2H), 2.7 (d and s, 4H), 1.5 (d, 2H); ir (KBr): 3.25, 6.25, 6.65, 8.05, 8.6, 12.5μ].

1. temperaturethe mixture then refluxed gently for 30 minutes
2. temperatureThe mixture was partially cooled
3. customevaporated to dryness
4. additionWater (50 ml.) was added to the residue, which
5. extractionextracted into ethyl acetate
6. dry with materialThe ethyl acetate was dried over anhydrous sodium sulfate
7. concentrationconcentrated to an oil, which
8. customcrystallized
9. filtrationTrituration with diethyl ether and filtration
10. customgave
11. custompurified 4-[2-(4-methoxyphenyl)-2-hydroxyethylthiomethyl]pyridine (1.50 g