Glycidoxypropyltrimethoxysilane → 1-Methoxycarbonyl-2-vinvlcyclopropane-1-carboxylic acid-[2-hydroxy-3-(3-trimethoxysilylpropoxy)propyl]ester

HRID 1636465Notes

Reaction equation

HRID 1636465 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:10]([OH:12])=[O:11])[CH2:7][CH:6]1[CH:8]=[CH2:9])=[O:4].[CH3:13][O:14][Si:15]([CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH:25]1[O:27][CH2:26]1)([O:18][CH3:19])[O:16][CH3:17].Cl([O-])(=O)(=O)=O.[Li+]>ClCCl>[OH:27][CH:25]([CH2:24][O:23][CH2:22][CH2:21][CH2:20][Si:15]([O:14][CH3:13])([O:16][CH3:17])[O:18][CH3:19])[CH2:26][O:12][C:10]([C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:7][CH:6]1[CH:8]=[CH2:9])=[O:11]

Participants

5

Reactant 3

HCID 17317GlycidoxypropyltrimethoxysilaneHCID 108559152-Vinylcyclopropane-1,1-dicarboxylic acid monomethyl esterHCID 23665649Lithium perchlorate

Product 1

HCID 536502661-Methoxycarbonyl-2-vinvlcyclopropane-1-carboxylic acid-[2-hydroxy-3-(3-trimethoxysilylpropoxy)propyl]esterYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10.0 g (58 mmol) 1-methoxycarbonyl-2-vinylcyclopropane carboxylic acid, 14.0 g trimethoxysilylpropylglycidyl-ether and 100 mg lithium perchlorate in 20 ml dichloromethane were stirred at room temperature for 15 days. After removal of solvent in vacuo, 20 g (83% yield) of a clear, yellow viscous liquid remained.

Workup

  1. customAfter removal of solvent in vacuo, 20 g (83% yield) of a clear, yellow viscous liquid

Sources & evidence

ORD record
ord-1f4adc3e9d2645b0ad6ccad56c1eab37
Source dataset
uspto-grants-2000_03
Patent number
US06034151

Reaction notes

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