4-((3-((Tert-butyldimethylsilyl)oxy)phenyl)(hydroxy)methyl)-N,N-diethylbenzamide → 4-(3-((tert-butyldimethylsilyl)oxy)benzoyl)-N,N-diethylbenzamide

HRID 1460108

反応式

HRID 1460108 の反応式
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Si:12]([O:19][C:20]1[CH:21]=[C:22]([CH:38]=[CH:39][CH:40]=1)[CH:23]([C:25]1[CH:37]=[CH:36][C:28]([C:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=1)[OH:24])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>ClCCl>[Si:12]([O:19][C:20]1[CH:21]=[C:22]([CH:38]=[CH:39][CH:40]=1)[C:23]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[O:30])=[CH:36][CH:37]=1)=[O:24])([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:14])[CH3:13]

参加物

4

反応物 2

HCID 223500144-((3-((Tert-butyldimethylsilyl)oxy)phenyl)(hydroxy)methyl)-N,N-diethylbenzamideHCID 178418287HCID 178418287、化合物

生成物 1

HCID 545736974-(3-((tert-butyldimethylsilyl)oxy)benzoyl)-N,N-diethylbenzamide収率 66.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Pyridinium chlorochromate (46.5 g, 0.216 mol) was added to a solution of 4-(3-(tert-butyldimethylsilyloxy)-α-hydroxybenzyl)-N,N-diethylbenzamide (44.6 g, 0.108 mol) from Example 11 in 600 mL dichloromethane at 0° C. The solution was stirred overnight at room temperature and filtered through Celite. The filtrate was concentrated to a volume of 150 mL and purified by chromatography on silica gel with ethyl acetate (5-40%) in hexane to give 29.4 g (66%) of 4-(3-((tert-butyldimethylsilyl)oxy)benzoyl)-N,N-diethylbenzamide as a white solid.

後処理

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated to a volume of 150 mL
  3. custompurified by chromatography on silica gel with ethyl acetate (5-40%) in hexane

出典と根拠

ORDレコード
ord-7a9207e51ffc44d2b2b0f9edd91e0877
出典データセット
uspto-grants-1998_12
特許番号
US05854249

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