Diethyl Malonate → Diethyl 2-vinylcyclopropane-1,1-dicarboxylate

HRID 2174439Notes

Reaction equation

HRID 2174439 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[CH2:5]Br.[C:7]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[OH-].[K+].[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC>ClCCl>[CH2:16]([O:15][C:7]([C:8]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH:4]1[CH:3]=[CH2:2])=[O:14])[CH3:17]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 14797Potassium HydroxideHCID 641245trans-1,4-Dibromo-2-buteneHCID 77620884Tricaprylylmethyl ammonium chloride

Product 1

HCID 111025Diethyl 2-vinylcyclopropane-1,1-dicarboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Patent Document 1 and Example 21 of Patent Document 2 describe that trans-1,4-dibromo-2-butene is allowed to react with diethyl malonate in dichloromethane in the presence of potassium hydroxide (90% flake form) and tricaprylylmethylammonium chloride, so as to obtain 1,1-di-ethoxycarbonyl-2-vinylcyclopropane at a yield of 89%.

Sources & evidence

ORD record
ord-29b86c7a8ab84cbfaaab475bfc5752d2
Source dataset
uspto-grants-2015_06
Patent number
US09061991B2

Reaction notes

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