反应详情

A solution of 2-chloro-3-methoxy-4-vinyl-6-(1-hydroxyethyl)-pyridine (485 mg, 2.27 mmol) in 10 mL of ethanol is treated with 485 mg of 20% palladium on carbon and 1,4-cyclohexadiene (2.0 mL, 21 mmol) and the reaction is refluxed for 4 h. The catalyst is removed by filtration through celite and the filter pad washed well with methanol. The filtrate is concentrated in vacuo and the residue is partitioned between 25 mL of saturated sodium bicarbonate and 4×25 mL of ethyl acetate. The combined organics are dried over potassium carbonate and concentrated in vacuo. The crude material is chromatographed over 20 g of silica gel (230-400 mesh), eluting with 100 mL of 50% ethyl acetate/hexanes followed by 80% ethyl acetate/hexanes to afford 256 mg (63%) of 3-methoxy-4-ethyl-6-(1-hydroxyethyl)-pyridine.

1. temperaturethe reaction is refluxed for 4 h
2. customThe catalyst is removed by filtration through celite
3. washthe filter pad washed well with methanol
4. concentrationThe filtrate is concentrated in vacuo
5. customthe residue is partitioned between 25 mL of saturated sodium bicarbonate and 4×25 mL of ethyl acetate
6. dry with materialThe combined organics are dried over potassium carbonate
7. concentrationconcentrated in vacuo
8. customThe crude material is chromatographed over 20 g of silica gel (230-400 mesh)
9. washeluting with 100 mL of 50% ethyl acetate/hexanes