Ketene dimethyl acetal → Ethyl (3,3-dimethoxycyclobutylidene)acetate

HRID 1476125Notes

Reaction equation

HRID 1476125 reaction equation
[CH3:1][O:2][C:3]([O:5][CH3:6])=[CH2:4].[C:7]([O:12][CH2:13][CH3:14])(=[O:11])[CH:8]=[C:9]=[CH2:10]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1([O:5][CH3:6])[CH2:10][C:9](=[CH:8][C:7]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4]1

Participants

4

Reactant 2

HCID 136706Ketene dimethyl acetalHCID 4066088Ethyl 2,3-butadienoate

Product 1

HCID 58288413Ethyl (3,3-dimethoxycyclobutylidene)acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.93 g (44.59 mmol) of 1,1-dimethoxyethene and 5 g (44.59 mmol) of ethyl buta-2,3-dienoate in 50 ml of toluene was heated at reflux and stirred for 24 h. After cooling to room temperature, the reaction mixture was freed from the solvent, and the crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 20:1). This gave 1.9 g (21% of theory) of the title compound as a colourless liquid which was used without further characterization for subsequent reactions.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-f7cb47885d63462faa1e80b80783e245
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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