反应详情

温度

100 °C

To a stirred solution of 2-(2-iodo-6-methylpyridin-3-yloxy)ethanol (350 g, 1.25 mol) in anhydrous DMF (3.5 L) was added NaH (60 g, 1.5 mol), Cu (33.7 g, 0.53 mol) and CuSO4 (100 g, 0.63 mol) at 0° C. After the addition, the mixture was stirred at 100° C. overnight. After cooling, the solvent was removed in vacuo and the residue was diluted with water (1.5 L). The aqueous solution was extracted with CH2Cl2 (3×350 mL). The combined organic layers were washed with brine (2×100 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified via column chromatography (silica gel, EtOAc/petroleum ether 1:20) to yield 6-methyl-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine (30.0 g, 16%) as a yellow oil.

1. additionAfter the addition
2. temperatureAfter cooling
3. customthe solvent was removed in vacuo
4. additionthe residue was diluted with water (1.5 L)
5. extractionThe aqueous solution was extracted with CH2Cl2 (3×350 mL)
6. washThe combined organic layers were washed with brine (2×100 mL)
7. dry with materialdried over anhydrous Na2SO4
8. concentrationconcentrated
9. customThe residue was purified via column chromatography (silica gel, EtOAc/petroleum ether 1:20)