Cornforth reagent → 3-(1-Nitro-2-naphthoyl)benzonitrile

HRID 1191303노트

반응식

HRID 1191303 반응식
[OH:1][CH:2]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[N+:21]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1[C:2]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])=[O:1])([O-:23])=[O:22]

참가 물질

4

반응물 2

HCID 2724130Cornforth reagentHCID 866904453-[Hydroxy(1-nitronaphthalen-2-yl)methyl]benzonitrile

생성물 1

HCID 866904463-(1-Nitro-2-naphthoyl)benzonitrile수율 86.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-[hydroxy(1-nitronaphthalen-2-yl)methyl]benzonitrile (7.37 g, 24.2 mmol) in dichloromethane (70 mL) was added silica gel (30 g) and pyridinium dichromate (13.7 g, 36.3 mmol), and stirred for 18 hours. The reaction mixture was filtered, and the residue was washed with chloroform. The filtrate was concentrated to dryness, and the residue was recrystallized from ethyl acetate, and washed with hexane to give the titled compound as a pale yellow crystal (6.32 g, yield 86%).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe residue was washed with chloroform
  3. concentrationThe filtrate was concentrated to dryness
  4. customthe residue was recrystallized from ethyl acetate
  5. washwashed with hexane

출처 및 근거

ORD 기록
ord-1419e081f6a949c6aec4ed7feba67278
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680110B2

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