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

HRID 535794ノート

反応式

HRID 535794 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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].

後処理

  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)

出典と根拠

ORDレコード
ord-5daf2dc1ccad4aef9c83a39ee4c1d25d
出典データセット
uspto-grants-2014_10
特許番号
US08859555B2

反応ノート

読み込み中…