Diethyl Malonate → Diethyl tetrahydropyran-4,4-dicarboxylate

HRID 1904390Notes

Reaction equation

HRID 1904390 reaction equation
O1CCC(C(O)=O)CC1.[CH2:10]([O:13][CH2:14][CH2:15]Cl)[CH2:11]Cl.[Na].[C:18]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>>[O:13]1[CH2:14][CH2:15][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])([C:18]([O:26][CH2:27][CH3:28])=[O:25])[CH2:11][CH2:10]1

Participants

5

Reactant 4

HCID 7761Diethyl MalonateHCID 8115Bis(2-chloroethyl) etherHCID 219302Oxane-4-carboxylic acidHCID 5360545Sodium

Product 1

HCID 239606Diethyl tetrahydropyran-4,4-dicarboxylate

Procedure

According to the statements in J. Chem. Soc., 2525-30 (1930) esters of tetrahydropyran-4-carboxylic acid can be prepared by treating 2,2'-dichlorodiethyl ether with the sodium salt of diethyl malonate to form diethyl tetrahydropyran-4,4-dicarboxylate, hydrolyzing to obtain tetrahydropyran-4,4-dicarboxylic acid, decarboxylating to tetrahydropyran-4-carboxylic acid, and finally esterifying.

Sources & evidence

ORD record
ord-a8c27a264e3d405fba7b285bb8635425
Source dataset
uspto-grants-1989_06
Patent number
US04837346

Reaction notes

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