Diisopropylethylamine → trans-3,3-Diethoxy-1,2-cyclobutanedicarboxylic acid, diethyl ester

HRID 377466

Reaction equation

HRID 377466 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:13]([O:15][C:16]([O:18]CC)=C)[CH3:14].[CH2:21](N(C(C)C)C(C)C)[CH3:22].[Cl-].[CH2:31]([Al+]CC(C)C)C(C)C>>[CH2:11]([O:10][C:1]1([O:9][CH2:21][CH3:22])[CH2:31][C@@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C@@H:2]1[C:16]([O:15][CH2:13][CH3:14])=[O:18])[CH3:12]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 1376731,1-DiethoxyetheneHCID 638144Diethyl fumarateHCID 16686353Diisobutyl aluminium chloride

Product 1

HCID 14378472trans-3,3-Diethoxy-1,2-cyclobutanedicarboxylic acid, diethyl ester

Procedure

By the method of Example 1, diethyl fumarate was reacted at -40° C. with 2 equivalents of ketene diethyl acetal in the presence of 0.2 equivalents of ethyldiisopropylamine and 2 equivalents of diisobutylaluminium chloride. 1H NMR analysis of the reaction mixture showed that the yield was quantitative.

Sources & evidence

ORD record
ord-f3657800254e48c1868601930e701594
Source dataset
uspto-grants-2000_02
Patent number
US06025519

Linked notes

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