反应详情

To a −78 C solution of 4-[1-Ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-benzoic acid methyl ester (2.50 g, 7.47 mmol) in THF (80 ml) is added lithium hexamethyldisilazide (8.22 ml, 8.22 mmol, 1.0 M in THF) and stirred at −78 C for 30 min. Cyclopentanone (730 μL, 8.22 mmol) is added and the reaction mixture warmed to room temperature. The reaction is quenched with saturated aqueous NH4Cl (30 ml) and concentrated. The residue is partitioned between EtOAc (300 ml) and 1.0N HCl (50 ml). The aqueous layer is extracted with EtOAc (100 ml). The combined organic layer are washed with water (50 ml), brine (50 ml), dried (MgSO4), concentrated and chromatographed (120 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (2.45 g, 79%).

1. customThe reaction is quenched with saturated aqueous NH4Cl (30 ml)
2. concentrationconcentrated
3. customThe residue is partitioned between EtOAc (300 ml) and 1.0N HCl (50 ml)
4. extractionThe aqueous layer is extracted with EtOAc (100 ml)
5. washThe combined organic layer are washed with water (50 ml), brine (50 ml)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. customchromatographed (120 g SiO2, 5% EtOAc/Hexanes)