反应详情

N-(6-Hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (0.625 g), triphenylphophine (0.786 g) and 4-trifluoromethyl-phenol (0.486 g) in toluene was treated at RT under an argon atmosphere with diisopropyl azodicarboxylate (0.67 g). The mixture was stirred for 2 h, partitioned between ice water and AcOEt, the layers were separated, the aqueous layer twice extracted with AcOEt. The combined organic layers were washed with water and saturated aqueous NaCl, dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt 100 to 85%) to give 2,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamide (0.98 g) as a yellow oil. MS (ESI): 353.2 (MH+).

1. custompartitioned between ice water and AcOEt
2. customthe layers were separated
3. extractionthe aqueous layer twice extracted with AcOEt
4. washThe combined organic layers were washed with water and saturated aqueous NaCl
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customThe residue was purified by flash chromatography (heptane/AcOEt 100 to 85%)