反应 #84772

反应方程式

N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamide

4-(4-bromo-3,5-dimethoxyphenyl)oxazole

LDA

→

1-(4-(4-bromo-3,5-dimethoxyphenyl)oxazol-2-yl)-2-methoxy-2-(4-morpholinophenyl)-ethanone

收率 34.0%

溶剂

THF

THF

反应条件

后处理

1. 1
   温度then cooled to −20° C
2. 2
   温度to slowly warm to room temperature
3. 3
   workup.STIRRINGstirred for a total of 21 hours
4. 4
   其他The reaction mixture was quenched with H2O
5. 5
   萃取extracted with EtOAc
6. 6
   洗涤The combined organics were washed with brine
7. 7
   干燥dried over Na2SO4
8. 8
   浓缩concentrated
9. 9
   其他Purification by chromatography (50-60% EtOAc-hexanes)

实验过程

To a −20° C. solution of 4-(4-bromo-3,5-dimethoxyphenyl)oxazole (0.158 g, 0.56 mmol) in anhydrous THF (2 mL) in an oven-dried flask under argon was added a solution of LDA (2.0 M in THF/heptane/ethylbenzene; 0.37 mL, 0.74 mmol) dropwise. The mixture was stirred at −20 to −10° C. for 50 min then cooled to −20° C. A solution of N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamide (0.245 g, 0.83 mmol) in anhydrous THF (3 mL) was added then the mixture was allowed to slowly warm to room temperature and stirred for a total of 21 hours. The reaction mixture was quenched with H2O and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated. Purification by chromatography (50-60% EtOAc-hexanes) provided 1-(4-(4-bromo-3,5-dimethoxyphenyl)oxazol-2-yl)-2-methoxy-2-(4-morpholinophenyl)-ethanone as a yellow solid (0.097 g, 34% yield). MS: m/z 517.1 [M+H]+.

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