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Water → 3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-one

HRID 85195
ノート
印刷プレビュー

反応式

HRID 85195 の反応式
CC(C)([O-])C.[K+].[Si:7]([O:24][CH2:25][C:26]1[C:27](=[O:32])[NH:28][CH:29]=[CH:30][CH:31]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:33][C:34]1[CH:39]=[C:38]([N+:40]([O-:42])=[O:41])[CH:37]=[CH:36][C:35]=1F.O>CN(C=O)C>[Si:7]([O:24][CH2:25][C:26]1[C:27](=[O:32])[N:28]([C:35]2[CH:36]=[CH:37][C:38]([N+:40]([O-:42])=[O:41])=[CH:39][C:34]=2[Cl:33])[CH:29]=[CH:30][CH:31]=1)([C:20]([CH3:23])([CH3:21])[CH3:22])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 23665647Potassium tert-butoxideHCID 594101563-({[tert-Butyl(diphenyl)silyl]oxy}methyl)pyridin-2(1H)-one

生成物 1

HCID 594101863-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

At 0° C., 0.500 g (4.46 mmol) of potassium tert-butoxide is added to 1.08 g (2.97 mmol) of the compound from Example 3A in 21 ml of DMF, and the mixture is stirred at room temperature for 30 min. 0.571 g (3.27 mmol) of 2-chloro-1-fluoro-4-nitrobenzene is added, and the mixture is stirred at RT. After 4.5 h, 200 ml of water are added, and the mixture is then extracted three times with ethyl acetate. The combined organic phases are washed with water and then dried over sodium sulphate. After filtration, the solvents are removed under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1). This gives 872 mg (56% of theory) of the desired compound.

後処理

  1. stirringthe mixture is stirred at RT
  2. waitAfter 4.5 h
  3. extractionthe mixture is then extracted three times with ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration
  7. customthe solvents are removed under reduced pressure
  8. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1)

出典と根拠

ORDレコード
ord-445897fbd85c41d594077132b150d2ba
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846934B2

反応ノート

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