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

HRID 1485439Notes

Reaction equation

HRID 1485439 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[C:5]([Si:9](Cl)([CH3:11])[CH3:10])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>ClCCl>[Si:9]([O:4][CH2:3][CH2:2][NH2:1])([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminoethanol (5 g, 82 mmol) and tert-butylchlorodimethylsilane (18 g, 123 mmol) in dichloromethane (200 mL) was added triethyl amine (16 g, 158 mmol) dropwise at 0° C. Once addition was completed, the resultant mixture was stirred at room temperature for 4 hours. The mixture was concentrated in vacuo to give a residue, and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give 2-(tert-butyldimethylsilyloxy)ethanamine as a colorless oil (12 g, 84%).

Workup

  1. additionOnce addition
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a residue
  4. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-3cd6b333c05f4cc9834ca144e628ca64
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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