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

HRID 1021472노트

반응식

HRID 1021472 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 67080588Tert-butoxy-2-(2-nitrovinyl)benzene수율 103.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e5521fc3af7f46b68c949a3e4e7ad976
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716498B2

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