Diethyl Malonate → Diethyl tetrahydropyran-4,4-dicarboxylate

HRID 2073328Notes

Reaction equation

HRID 2073328 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[CH2:14][CH2:15][O:16][CH2:17][CH2:18]Cl>C(O)C>[CH2:11]([O:10][C:2]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:9])[CH3:12]

Participants

5

Reactant 3

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

Product 1

HCID 239606Diethyl tetrahydropyran-4,4-dicarboxylateYield 26.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (10 g) was dissolved in dry ethanol (300 cm3) and then diethyl malonate (30 g) was added slowly. After stirring for 15 minutes, bis(2-chloroethyl)ether (35 g) was added dropwise. The mixture was heated under reflux for 72 hours and then cooled to room temperature. After filtering the solvent was removed from the reaction mixture under reduced pressure to give the crude product. An initial purification was achieved by chromatography on alumina (activity 4) using ethyl acetate/petroleum ether mixtures as eluants. The pure product (11.3 g) was isolated by distillation under reduced pressure as an oil (b.p. 106°-108° C. at 0.03 mmHg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 72 hours
  3. filtrationAfter filtering the solvent
  4. customwas removed from the reaction mixture under reduced pressure
  5. customto give the crude product
  6. customAn initial purification

Sources & evidence

ORD record
ord-21db3d7b742542b3a01126f1867b4bc2
Source dataset
uspto-grants-1990_04
Patent number
US04916214

Reaction notes

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