Acetic Acid → 4-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine

HRID 77898

反応式

HRID 77898 の反応式
C(O)(=O)C.[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)[CH:7]=1.[N+:22]([CH3:25])([O-:24])=[O:23].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17](/[CH:18]=[CH:25]/[N+:22]([O-:24])=[O:23])=[CH:16][CH:15]=2)[CH:7]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 592554674-(4-Methyl-pyridin-2-yloxymethyl)-benzaldehyde

生成物 1

HCID 592551344-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine収率 109.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To an acetic acid (20.0 mL) solution of 4-(4-methyl-pyridin-2-yloxymethyl)-benzaldehyde (2.60 g, 11.5 mmol) described in Manufacturing Example 43-1-2 were added nitromethane (3.50 g, 57.3 mmol) and ammonium acetate (1.76 g, 22.9 mmol) at room temperature under nitrogen atmosphere, which was stirred for 4 hours at 100° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was separated, 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 (3.40 g) as a crude product.

後処理

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

出典と根拠

ORDレコード
ord-cc6dd927238f4dbab11b01f4a7bf78c3
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

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