Imidazole → 4-[(tert-Butyldimethylsilyl)oxy]-N-methylaniline

HRID 63659

反応式

HRID 63659 の反応式
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH3:10][C:11]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.O>C(Cl)Cl>[Si:14]([O:9][C:6]1[CH:7]=[CH:8][C:3]([NH:2][CH3:1])=[CH:4][CH:5]=1)([C:11]([CH3:13])([CH3:12])[CH3:10])([CH3:16])[CH3:15]

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 5931n-Methyl-p-aminophenolHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 134173524-[(tert-Butyldimethylsilyl)oxy]-N-methylaniline収率 43.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-(methylamino)phenol (5.0 g, 29 mmol), TBDMSCl (4.8 g, 32 mmol) and imidazole (9.9 g, 0.15 mol) in DCM was stirred at r.t. for 1 h. Water was added, and the mixture was extracted with EtOAc. The organic layer was dried (Na2SO4), concentrated and purified by silica gel chromatography (PE:EtOAc=10:1) to give 3.0 g (43%) of the title compound as a dark green oil. [M+H] Calc'd for C13H23NOSi, 238. Found, 238.

後処理

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (PE:EtOAc=10:1)

出典と根拠

ORDレコード
ord-5dd49465ed79419d95b3eac04ff6c8cb
出典データセット
uspto-grants-2016_09
特許番号
US09447046B2

関連ノート

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