반응 #84772

반응 방정식

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

수율 34.0%

용매

THF

THF

반응 조건

후처리

1. 1
   온도then cooled to −20° C
2. 2
   온도to slowly warm to room temperature
3. 3
   workup.STIRRINGstirred for a total of 21 hours
4. 4
   기타The reaction mixture was quenched with H2O
5. 5
   추출extracted with EtOAc
6. 6
   세척The combined organics were washed with brine
7. 7
   건조dried over Na2SO4
8. 8
   농축concentrated
9. 9
   기타Purification by chromatography (50-60% EtOAc-hexanes)

실험 절차

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]+.

출처