反应详情

To a stirred solution of ethyl 2-methyl nicotinate (1.04 g, 6.30 mmol) in dry THF (30 mL) was slowly added EtMgBr (3.0 M in Et2O, 5.2 mL, 16 mmol). The mixture was warmed to reflux and stirred for 60 h under N2. The suspension was cooled, poured into ice (50 mL) and stirred for 3 h. The layers were separated, and the aqueous layer was extracted with Et2O (5×100 mL). The combined organic layers were dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (1:1 Et2O/CH2Cl2), affording 3-(2-methyl-pyridin-3-yl)-pentan-3-ol as a yellow solid (0.447 g, 40%). 1H NMR (CDCl3) δ 0.77 (t, 6H, J=7.5 Hz), 1.80-2.12 (m, 4H), 2.70 (s, 3H), 7.12 (dd, 1H, J=4.8, 7.8 Hz), 7.87 (dd, 1H, J=7.8, 1.5 Hz), 8.39 (dd, 1H, J=4.8, 1.5 Hz).

1. temperatureThe mixture was warmed
2. temperatureto reflux
3. temperatureThe suspension was cooled
4. stirringstirred for 3 h
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with Et2O (5×100 mL)
7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
8. filtrationAfter filtration the solvent
9. customwas removed by evaporation under vacuum
10. customthe residue was purified by flash chromatography on a silica gel column (1:1 Et2O/CH2Cl2)