反应详情

To a stirred solution of 1-(6-bromo-2-pyridinyl)-1-pentanol (2.00 g, 8.19 mmol) and ethyl (4-hydroxy-2-methylphenoxy)acetate (1.89 g, 8.99 mmol) in dry THF (160 mL) at 0° C. (ice/water bath) under nitrogen was added ADDP (4.13 g, 16.37 mmol) portion-wise over 5 min followed by nBu3P (1.07 mL, 4.30 mmol) drop-wise over 1-2 min. The mixture was stirred with slow warming to rt over 21 h and then concentrated under vacuum, diluted with EtOAc (300 mL) and washed with water (200 mL). The aqueous layer was then re-extracted with EtOAc (300 mL) and the combined organic layer washed with brine (350 mL), dried (MgSO4), filtered and reduced to give a orange solid residue. Purification by SPE (silica, 20 g Cartridge) eluting with cyclohexane:EtOAc (gradient 1:0 to 1:1) afforded the title compound (2.31 g).

1. concentrationconcentrated under vacuum
2. additiondiluted with EtOAc (300 mL)
3. washwashed with water (200 mL)
4. extractionThe aqueous layer was then re-extracted with EtOAc (300 mL)
5. washthe combined organic layer washed with brine (350 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customto give a orange solid residue
9. customPurification by SPE (silica, 20 g Cartridge)
10. washeluting with cyclohexane