Nitromethane → 1-Butoxy-4-((E)-2-nitro-vinyl)-benzene

HRID 77976

반응식

HRID 77976 반응식
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[N+:14]([CH3:17])([O-:16])=[O:15].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9](/[CH:10]=[CH:17]/[N+:14]([O-:16])=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 6375NitromethaneHCID 798134-ButoxybenzaldehydeHCID 517165Ammonium Acetate

생성물 1

HCID 62679031-Butoxy-4-((E)-2-nitro-vinyl)-benzene수율 76%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-butoxy-benzaldehyde (4.72 g, 26.5 mmol) described in Manufacturing Example 67-1-1, nitromethane (2.85 mL, 53 mmol), ammonium acetate (3.06 g, 39.8 mmol) and acetic acid (40 mL) was stirred for 13 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (4.44 g, 76%).

후처리

  1. temperatureThis mixture was cooled to room temperature
  2. concentrationconcentrated under a reduced pressure
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1)

출처 및 근거

ORD 기록
ord-b967ff8d1d954a9fbb72e99a5a4b2299
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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