Diethyl Malonate → Diethyl tetrahydropyran-4,4-dicarboxylate

HRID 635529

Reaction equation

HRID 635529 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br>C(O)C>[O:19]1[CH2:20][CH2:21][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])([C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 21521Bis(2-bromoethyl) etherHCID 2723922Sodium ethoxide

Product 1

HCID 239606Diethyl tetrahydropyran-4,4-dicarboxylateYield 61.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl malonate (32.0 g) was added to a solution of sodium ethoxide (1 equivalent) in ethanol and the solution was stirred for 30 min. 2-Bromoethylether (46.0 g) was then added and the mixture was stirred at reflux for 3 h. The mixture was then cooled, evaporated in vacuo and the residue partitioned between water and dichloromethane. The organic layer was separated and washed with water and brine, then dried (MgSO4) and evaporated. The residue was then purified by flash column chromatography on silica gel, eluting with 4:1 hexanes/ether, to give the title compound (28.0 g) as colourless liquid.

Workup

  1. stirringthe mixture was stirred
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was then cooled
  4. customevaporated in vacuo
  5. customthe residue partitioned between water and dichloromethane
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was then purified by flash column chromatography on silica gel
  11. washeluting with 4:1 hexanes/ether

Sources & evidence

ORD record
ord-b5ba0cde8b0043e7a597f969f5f28474
Source dataset
uspto-grants-2001_02
Patent number
US06187924B1

Linked notes

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