反应详情

Sodium borohydride (11.30 g, 299 mmol) was added to a solution of the methyl 6-methoxynicotinate (5.00 g, 29.9 mmol) in ethanol (100 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred for 3 days. The reaction was cooled to 0° C. and quenched by slow addition of 1 N HCl until pH 4.0. The reaction mixture was concentrated to remove ethanol. The remaining aqueous solution was washed with ethyl acetate (2×), then neutralized with saturated aqueous sodium bicarbonate, then extracted with ethyl acetate (3×). The organic layers were combined, washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was purified by silica chromatography (hexanes/ethyl acetate 1:1, 3:7) to give a clear oil. Mass/Yield-3.9 g/94% TLC (hexanes/ethyl acetate=1:1) Rf=0.22, UV active. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.91 (s, 3 H) 4.61 (s, 2 H) 6.68-6.77 (m, 1 H) 7.49-7.68 (m, 1 H) 8.09 (s, 1 H).

1. temperatureThe reaction was cooled to 0° C.
2. customquenched by slow addition of 1 N HCl until pH 4.0
3. concentrationThe reaction mixture was concentrated
4. customto remove ethanol
5. washThe remaining aqueous solution was washed with ethyl acetate (2×)
6. extractionextracted with ethyl acetate (3×)
7. washwashed with brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude material was purified by silica chromatography (hexanes/ethyl acetate 1:1, 3:7)
12. customto give a clear oil