反应详情

To a suspension of 75 mg (0.21 mmol) of aldehyde 3-1 in THF at −78° C. was added 80 μL (0.25 mmol) of methyl magnesium bromide solution (3M in Et2O). After stirring 1 h at that temperature, an additional 80 μL of the Grignard reagent was added and stirring was continued for 1 h more. The reaction was quenched with saturated NH4Cl, partitioned between brine and EtOAc, the organic phase washed with brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 5-1 as a white solid. Data for 5-1: 1HNMR (500 MHz, CDCl3) δ 7.6 (m, 2H), 7.4-7.2 (m, 3H), 7.1-6.9 (m, 3H), 6.5 (s, 1H), 5.05 (m, 1H), 4.8 (m, 1H), 4.6 (m, 1H), 4.35 (m, 1H), 2.8 (s, 6H), 1.4 (m, 3H) ppm. HRMS (ES) calc'd M+H for C21H22F2N2O2: 373.1722. Found: 373.1713.

1. stirringstirring
2. waitwas continued for 1 h
3. customThe reaction was quenched with saturated NH4Cl
4. custompartitioned between brine and EtOAc
5. washthe organic phase washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe residue was purified by column chromatography on silica gel with EtOAc/hexanes