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

HRID 2169188Notes

Reaction equation

HRID 2169188 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-8a393f0f8fea41e7845dd465a3530688
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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