Nitromethane → 2-(3-((E)-2-nitro-vinyl)-phenoxymethyl)-pyridine

HRID 77947

反応式

HRID 77947 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O.[N+:17]([CH3:20])([O-:19])=[O:18].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[N+:17](/[CH:20]=[CH:12]/[C:11]1[CH:10]=[C:9]([CH:16]=[CH:15][CH:14]=1)[O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([O-:19])=[O:18]

参加物

5

反応物 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 64838053-(Pyridin-2-ylmethoxy)benzaldehyde

生成物 1

HCID 592552492-(3-((E)-2-nitro-vinyl)-phenoxymethyl)-pyridine収率 71.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-(pyridin-2-ylmethoxy)-benzaldehyde (2.98 g, 14 mmol) described in Manufacturing Example 60-1-1, nitromethane (1.51 mL, 28 mmol), ammonium acetate (1.62 g, 21 mmol) and acetic acid (30 mL) was stirred for 6 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, 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=4:1-2:1-1:1) to obtain the title compound (2.56 g, 71%).

後処理

  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
  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=4:1-2:1-1:1)

出典と根拠

ORDレコード
ord-320a051a5f1243e4b9c52dd49a11aefc
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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