Acetic Acid → 2-(3,4-Dichlorophenyl)-5-(2-nitrovinyl)furan

HRID 872429

반응식

HRID 872429 반응식
C(O)(=O)C.C(N)CC.C([O-])(=O)C.C([NH3+])CC.[Cl:17][C:18]1[CH:19]=[C:20]([C:25]2[O:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)[CH:21]=[CH:22][C:23]=1[Cl:24].[N+:32]([CH3:35])([O-:34])=[O:33]>CO>[Cl:17][C:18]1[CH:19]=[C:20]([C:25]2[O:31][C:28](/[CH:29]=[CH:35]/[N+:32]([O-:34])=[O:33])=[CH:27][CH:26]=2)[CH:21]=[CH:22][C:23]=1[Cl:24]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 6375NitromethaneHCID 7852PropylamineHCID 6176885-(3,4-Dichlorophenyl)-2-furaldehydeHCID 22348537n-Propylammonium acetate

생성물 1

HCID 8976012-(3,4-Dichlorophenyl)-5-(2-nitrovinyl)furan수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

A stirred solution of acetic acid (1.4 ml, 1.46 g, 24.3 mmol) in methanol (3.5 ml) under nitrogen atmosphere at 0° C. was treated dropwise with n-propylamine (2.0 ml, 1.42 g, 24.0 mmol). The resulting n-propylammonium acetate solution was stirred at 0° C. for 5 min, then added dropwise to a stirred solution of 5-(3,4-dichlorophenyl)furfural (10.04 g, 41.6 mmol) in nitromethane (6.8 ml, 7.61 g, 124.7 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 30 min. Then the cooling bath was removed, and stirring was continued at RT. From time to time, 10 ml of THF was added five times. After stirring overnight THF was evaporated and water was added. A solid was filtrated, washed with water and heptane to afford 11.46 g of 2-(3,4-dichlorophenyl)-5-((E)-2-nitrovinyl)furan. 1H NMR (400 MHz, DMSO-d6): 7.38 (1H, d), 7.43 (1H, d), 7.76 (1H, d), 7.95 (1H, dd), 8.03 (1H, d), 8.19 (1H, d), 8.31 (1H, d)

후처리

  1. customThen the cooling bath was removed
  2. stirringstirring
  3. customwas continued at RT
  4. additionFrom time to time, 10 ml of THF was added five times
  5. stirringAfter stirring overnight THF
  6. customwas evaporated
  7. additionwater was added
  8. filtrationA solid was filtrated
  9. washwashed with water and heptane

출처 및 근거

ORD 기록
ord-02b842f831f0463fb14cebfedd74b007
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975254B2

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