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

HRID 2169188

反応式

HRID 2169188 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8a393f0f8fea41e7845dd465a3530688
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

関連ノート

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