Nitromethane → Tert-butoxy-2-(2-nitrovinyl)benzene

HRID 1021472ノート

反応式

HRID 1021472 の反応式
[C:1]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[N+:14]([CH3:17])([O-:16])=[O:15].Cl.CN.C([O-])(=O)C.[Na+]>ClCCl.O>[C:1]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[CH:17][N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 149555262-tert-Butoxybenzaldehyde

生成物 1

HCID 67080588Tert-butoxy-2-(2-nitrovinyl)benzene収率 103.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

2-tert-Butoxybenzaldehyde (550 mg, 3.09 mmol) was treated with nitromethane (1167 μL, 21.6 mmol) at ambient temperature in a flask. Solid methylamine hydrochloride (133 mg, 1.98 mmol) and sodium acetate (162 mg, 1.98 mmol) were added and the colorless reaction mixture was stirred rapidly at ambient temperature. After 30 minutes, the reaction mixture started to turn yellow. After 16 hours, the reaction was very yellow and precipitate has formed. Water (20 ml) and dichloromethane (40 ml) were added and the layers partitioned. The dichloromethane layer was dried with sodium sulfate, filtered, and concentrated to provide the title compound (705 mg, 3.19 mmol, 103% yield) as a yellow oil.

後処理

  1. waitAfter 16 hours
  2. customprecipitate has formed
  3. customthe layers partitioned
  4. dry with materialThe dichloromethane layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-e5521fc3af7f46b68c949a3e4e7ad976
出典データセット
uspto-grants-2014_05
特許番号
US08716498B2

反応ノート

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