Water → N-(2-((tert-butyldimethylsilyl)oxy)ethyl)aniline

HRID 2169188

반응식

HRID 2169188 반응식
[C:1]1([NH:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].O>ClCCl>[Si:20]([O:10][CH2:9][CH2:8][NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

참가 물질

6

반응물 4

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 31235N-(2-Hydroxyethyl)anilineHCID 81531Diisopropylethylamine

생성물 1

HCID 21993569N-(2-((tert-butyldimethylsilyl)oxy)ethyl)aniline수율 46.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2-(phenylamino)ethanol (10 g, 72.9 mmol, Eq: 1.00) in dichloromethane (200 ml) were added diisopropylethylamine (13.2 g, 17.8 ml, 102 mmol, Eq: 1.4) followed by tert-butyldimethylsilyl chloride (11.0 g, 72.9 mmol, Eq: 1.00) at room temperature under a nitrogen atmosphere. The resulting solution was stirred for 16 hrs and then it was poured into water (200 ml) and the organic layer was separated, washed with brine, dried (MgSO4), concentrated, and chromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane) to obtain N-(2-(tert-butyldimethylsilyloxy)ethyl)aniline (46) (8.45 g, 33.6 mmol, 46.1% yield).

후처리

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-8a393f0f8fea41e7845dd465a3530688
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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