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

HRID 1691082ノート

反応式

HRID 1691082 の反応式
[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]

参加物

5

反応物 3

HCID 6375NitromethaneHCID 798134-ButoxybenzaldehydeHCID 517165Ammonium Acetate

生成物 1

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

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 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%).

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 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)

出典と根拠

ORDレコード
ord-466e87816d744e0fa4395da6629f7236
出典データセット
uspto-grants-2012_04
特許番号
US08153662B2

反応ノート

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