Diethyl Malonate → Diethyl tetrahydropyran-4,4-dicarboxylate

HRID 49040

Reaktionsgleichung

Reaktionsgleichung von HRID 49040
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 239606Diethyl tetrahydropyran-4,4-dicarboxylateAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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-Bromoethyl ether (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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-eedaf22714fd417fb04112ffc63e919e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706719B1

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