Nitromethane → (E)-1-((2-methoxyethoxy)methoxy)-4-(2-nitrovinyl)benzene

HRID 535794노트

반응식

HRID 535794 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[CH3:16][N+:17]([O-:19])=[O:18]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11](/[CH:12]=[CH:16]/[N+:17]([O-:19])=[O:18])=[CH:10][CH:9]=1

참가 물질

4

반응물 2

HCID 6375NitromethaneHCID 11401561Benzaldehyde, 4-[(2-methoxyethoxy)methoxy]-2회

생성물 1

HCID 67064875(E)-1-((2-methoxyethoxy)methoxy)-4-(2-nitrovinyl)benzene수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 4-((2-methoxyethoxy)methoxy)benzaldehyde (Intermediate I, 1.86 g, 8.85 mmol) and NH4OAc (0.75 g, 9.73 mmol) in dry THF (15 mL) and CH3NO2 (15 mL) was refluxed for 20 h and allowed to reach room temperature. The volume of the reaction was reduced to aprox. ⅓, by rotatory evaporation; the resulting solution was poured into water (15 mL) and extracted with AcOEt (2×15 mL). The organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residual brown oil was purified by column chromatography on silica gel (15-30% EtOAc/Hexanes) affording 1.77 g of (E)-1-((2-methoxyethoxy)methoxy)-4-(2-nitrovinyl)benzene [Rf=0.7 (50% AcOEt/Hexanes), yellow solid, 79% yield].

후처리

  1. temperaturewas refluxed for 20 h
  2. customto reach room temperature
  3. custom⅓, by rotatory evaporation
  4. additionthe resulting solution was poured into water (15 mL)
  5. extractionextracted with AcOEt (2×15 mL)
  6. washThe organic layers were washed with brine (20 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customAfter removal of the solvent
  10. customthe residual brown oil was purified by column chromatography on silica gel (15-30% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-5daf2dc1ccad4aef9c83a39ee4c1d25d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859555B2

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