Dimethyl malonate → HCID 20505507, compound

HRID 2118112Notes

Reaction equation

[C:1]([O:10][CH3:11])(=[O:9])[C:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])=[CH2:3].[Na].[C:13]([O:20][CH3:21])(=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16].[H-].[Na+]>>[CH:14]([C:13]([O:20][CH3:21])=[O:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:3][CH:2]([C:1]([O:10][CH3:11])=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

Reactant 4

HCID 7943Dimethyl malonate2×

HCID 24758Sodium hydride

HCID 69240Dimethyl itaconate

HCID 5360545Sodium

Product 1

HCID 20505507HCID 20505507, compound

Procedure

Conventionally, a method for producing cyclopentanone-2,3,5-tricarboxylic acid triester, which is comprised of allowing dimethyl itaconate to react with sodium salt of dimethyl malonate that is prepared from sodium hydride and dimethyl malonate, isolating a product (tetramethyl 1,1,3,4-butanetetracarboxylate) from resulting reaction mixture by purification with distillation after neutralizing with an acid, and then cyclizing the product in the presence of not less than one equivalent of sodium methoxide, and isolating a target compound from resultant reaction mixture after neutralizing with an acid, has been known (see U.S. Pat. No. 4,272,437, columns 361-362).

Sources & evidence

ORD record: ord-56261d36446f4764a8855b5d016fbf18
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442827B2

Reaction notes

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