Diethyl Malonate → Diethyl tetrahydropyran-4,4-dicarboxylate

HRID 1080443Notes

Reaction equation

HRID 1080443 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6]Cl)[CH2:2]Cl.[Na].[C:9]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>>[O:4]1[CH2:5][CH2:6][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:9]([O:17][CH2:18][CH3:19])=[O:16])[CH2:2][CH2:1]1

Participants

4

Reactant 3

HCID 7761Diethyl MalonateHCID 8115Bis(2-chloroethyl) etherHCID 5360545Sodium

Product 1

HCID 239606Diethyl tetrahydropyran-4,4-dicarboxylate

Procedure

From J. Chem. Soc. 1930, pages 2525 to 2530, a process for preparing tetrahydropyran-4-carboxylic acid esters is known in which β,β'-dichlorodiethyl ether is reacted with the sodium salt of diethyl malonate to give diethyl tetrahydropyran-4,4-dicarboxylate, and this is converted to tetrahydropyran-4-carboxylic acid via tetrahydropyran-4,4-dicarboxylic acid and finally esterified to give the desired tetrahydropyran-4-carboxylic acid ester.

Sources & evidence

ORD record
ord-e464af1cd2a249209d009be49abb95fc
Source dataset
uspto-grants-1996_12
Patent number
US05580994

Reaction notes

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