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

HRID 63659

반응식

HRID 63659 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5dd49465ed79419d95b3eac04ff6c8cb
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447046B2

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