反应详情

4-(Hydroxymethyl)-1-methyl-1,2,3,6-tetrahydropyridine (D1, 5.63 g, 0.044 mol), 2-iodophenol (7.80 g, 0.035 mol) and triphenylphosphine (11.61 g, 0.044 mol) were stirred in dry THF (200 ml) under Ar as diethyl azodicarboxylate (7.0 ml, 0.044 mol) was added portionwise. The solution was stirred for 1 h, concentrated, diluted with ethyl acetate, and extracted with dil. HCl. The extract was basified (sat. K2CO3 solution) and extracted with ethyl acetate. This organic extract was dried (Na2SO4) and evaporated to give a brown oil. Purification by chromatography on silica gel, eluting with 0-10% methanol/chloroform (gradient) gave the title compound (7.65 g, 65%) as an amber oil.

1. additionwas added portionwise
2. concentrationconcentrated
3. additiondiluted with ethyl acetate
4. extractionextracted with dil. HCl
5. extractionextracted with ethyl acetate
6. extractionThis organic extract
7. dry with materialwas dried (Na2SO4)
8. customevaporated
9. customto give a brown oil
10. customPurification by chromatography on silica gel
11. washeluting with 0-10% methanol/chloroform (gradient)