Diethyl Oxalate → HCID 86734794, compound

HRID 2399089Notes

Reaction equation

HRID 2399089 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH:11]1[C:15](=[O:16])[C:14](=[O:17])[CH2:13][C:12]1=[O:18])([O:3][CH3:4])=[O:2].CC1(CCC#C)OCCO1.O=C(C)CCC#CCCCC(O)=O.O=C(C)CCC#CCCCC(OC)=O.O=C(C)CC/C=C\CCCC([O-])=O.O=C(C)CC/C=C\CCCC(OC)=O.[C:83](OCC)(=[O:89])[C:84]([O:86][CH2:87][CH3:88])=[O:85]>>[C:1]([CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH:11]1[C:15](=[O:16])[C:14](=[O:17])[CH:13]([C:83]([C:84]([O:86][CH2:87][CH3:88])=[O:85])=[O:89])[C:12]1=[O:18])([O:3][CH3:4])=[O:2]

Participants

8

Reactant 7

HCID 7268Diethyl OxalateHCID 10034704HCID 10034704, compoundHCID 21432375HCID 21432375, compoundHCID 21432376HCID 21432376, compoundHCID 23261195HCID 23261195, compoundHCID 68120576HCID 68120576, compoundHCID 86734795HCID 86734795, compound

Product 1

HCID 86734794HCID 86734794, compound

Procedure

In a process for the synthesis of 2-(6-carbomethoxy-cis-hexenyl)-cyclopentane-1,3,4-trione by stepwise converting 2-methyl-2-(3-butynyl)-1,3-dioxolane to 9-oxo-5-decynoic acid, esterifying that acid to methyl 9-oxo-5-decynoate, reducing the latter to 9-oxo-cis-5-decenoate, condensing the methyl 9-oxo-cis-5-decenoate with diethyl oxalate to obtain 2-(6-carbomethoxy-cis-2-hexenyl)-5-ethoxalyl-cyclopentane-1,3,4-trione as an intermediate, and hydrolyzing the intermediate to obtain 2-(6-carbomethoxy-cis-hexenyl)-cyclopentane-1,3,4-trione, the improvement which comprises:

Sources & evidence

ORD record
ord-b1680ff5d95b4658a3f43471413f72cd
Source dataset
uspto-grants-1977_05
Patent number
US04026911

Reaction notes

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