Ethanolamine → (2-Aminoethoxy)(tert-butyl)dimethylsilane

HRID 2169315Notes

Reaction equation

HRID 2169315 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].C(N(CC)C(C)C)(C)C.[C:14]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])([CH3:16])[CH3:15].O>ClCCl>[Si:18]([O:4][CH2:3][CH2:2][NH2:1])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneYield 99.44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-amino-ethanol (55 g, 900.46 mmol) in dichloromethane (1000 mL) were added N,N-diisopropylethylamine (220 mL, 1260.64 mmol) and tert-butyl-chloro-dimethyl-silane (135.7 g, 900.46 mmol) at 0° C. followed by stirring for 16 h at room temperature. After completion of the reaction, water (500 mL) was added and the resulting mixture extracted with dichloromethane. The separated organic part was washed with water (2×100 mL) and brine (100 mL) and dried and concentrated to get 2-(tert-butyl-dimethylsilanyloxy)-ethylamine (8c) (157 g, 99.44%) as a light yellow oil.

Workup

  1. additionwas added
  2. extractionthe resulting mixture extracted with dichloromethane
  3. washThe separated organic part was washed with water (2×100 mL) and brine (100 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-98480cba71bc43feab73d3bf27086483
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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