反应详情

温度

-78 °C

To a solution of 2-(4-bromo-3,5-dimethoxyphenyl)furan (0.203 g, 0.72 mmol) in anhydrous THF (2 mL) under argon in an oven-dried flask cooled to −78° C. was added a solution of lithium diisopropylamide (2.0 M in THF/heptane/ethylbenzene; 0.4 mL, 0.8 mmol) dropwise. After stirring for 35 min at −78° C., a solution of N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamide (0.315 g, 1.1 mmol) in THF (2 mL) was added dropwise. After stirring for 25 min, the mixture was allowed to warm to room temp while stirring for 2 hrs. The reaction was quenched with the addition of saturated aqueous NH4Cl then brine and EtOAc were added. The layers were separated and the organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by column chromatography (35-65% EtOAc-hexanes) provided an oil that was triturated with MeOH-Et2O (1:1) with sonication. The solid was collected on a Büchner, rinsed with MeOH-Et2O (1:1) and dried in vacuo to give 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone as a yellow solid. A second batch was collected from MeOH-Et2O (˜10%) to give additional product (0.220 g total, 59% yield). MS: m/z 516.1 [M+H]+.

1. stirringAfter stirring for 25 min
2. temperatureto warm to room temp
3. stirringwhile stirring for 2 hrs
4. customThe reaction was quenched with the addition of saturated aqueous NH4Cl
5. additionbrine and EtOAc were added
6. customThe layers were separated
7. washthe organic layer was washed with brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated in vacuo
10. customPurification by column chromatography (35-65% EtOAc-hexanes)
11. customprovided an oil that
12. customwas triturated with MeOH-Et2O (1:1) with sonication
13. customThe solid was collected on a Büchner
14. washrinsed with MeOH-Et2O (1:1)
15. customdried in vacuo