Nitromethane → 2-Benzyl-5-((E)-2-nitro-vinyl)-pyridine

HRID 640541ノート

反応式

HRID 640541 の反応式
[CH2:1]([C:8]1[N:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:16]([CH3:19])([O-:18])=[O:17].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11](/[CH:14]=[CH:19]/[N+:16]([O-:18])=[O:17])=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 216983476-Benzyl-pyridine-3-carbaldehyde

生成物 1

HCID 592553902-Benzyl-5-((E)-2-nitro-vinyl)-pyridine収率 21%

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 6-benzyl-pyridine-3-carbaldehyde (4.7 g, 24 mmol) described in Manufacturing Example 210-1-4, nitromethane (7.3 g, 120 mmol), ammonium acetate (5.6 g, 72 mmol), and acetic acid (40 mL) was stirred for 90 minutes at 100° C. The reaction solution was partitioned into ethyl acetate and water. The organic layer was washed with saturated aqueous sodium bicarbonate and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (1.2 g, 21%).

後処理

  1. customThe reaction solution was partitioned into ethyl acetate and water
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-06055bd1fdc74074b556c058f6a556e8
出典データセット
uspto-grants-2010_04
特許番号
US07691882B2

反応ノート

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