Acetic Acid → 2-(2-Fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)pyridine

HRID 640338노트

반응식

HRID 640338 반응식
C(O)(=O)C.[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH:9]=O.[N+:22]([CH3:25])([O-:24])=[O:23].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[F:5][C:6]1[CH:7]=[C:8](/[CH:9]=[CH:25]/[N+:22]([O-:24])=[O:23])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 592552243-Fluoro-4-(pyridin-2-ylmethoxy)-benzaldehyde

생성물 1

HCID 592551412-(2-Fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)pyridine수율 90.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

To an acetic acid (25.0 mL) solution of 3-fluoro-4-(pyridin-2-ylmethoxy)-benzaldehyde (2.80 g, 12.1 mmol) described in Manufacturing Example 87-1-1 were added nitromethane (3.69 g, 60.5 mmol) and ammonium acetate (1.87 g, 24.2 mmol) under nitrogen atmosphere at room temperature, which was stirred for 2 hours at 110° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted 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 to obtain the title compound (3.00 g) as a crude product.

후처리

  1. extractionthe organic layer was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure

출처 및 근거

ORD 기록
ord-15c43e1545ea4e598019811c5a312951
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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