Diethyl Malonate → Diethyl tetrahydropyran-4,4-dicarboxylate

HRID 1350105Notes

Reaction equation

HRID 1350105 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>[O:16]1[CH2:17][CH2:18][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])([C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:14][CH2:15]1

Participants

5

Reactant 3

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

Product 1

HCID 239606Diethyl tetrahydropyran-4,4-dicarboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (20.7 g, 900 mmol) was carefully dissolved in dry ethanol (300 mL) and to this mixture was added diethyl malonate (144 g, 900 mmol) and 2, bis-(2-chloroethyl)ether (129 g, 900 mmol). The reaction mixture was refluxed for 15 h and cooled to room temperature. The solvent was removed by rotary evaporation, the product acidified with 10% HCl (200 mL), extracted with ethyl acetate (4×200 mL) and dried (Na2SO4). Removal of solvent by rotary evaporation, followed by distillation (170–175° C., 22 mm Hg) furnished the product (98.0 g, 48% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. customThe solvent was removed by rotary evaporation
  3. extractionextracted with ethyl acetate (4×200 mL)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of solvent
  6. customby rotary evaporation
  7. distillationfollowed by distillation (170–175° C., 22 mm Hg)

Sources & evidence

ORD record
ord-0f4e499d51114c2f82c241bd00eae1c3
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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