Diethyl Ether → 2-[6-(Tetrahydro-pyran-2-yloxy)-hexyl]-malonic acid diethyl ester

HRID 500063

Reaktionsgleichung

Reaktionsgleichung von HRID 500063
[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][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.CCOCC>C(O)C>[CH2:11]([O:10][C:2](=[O:9])[CH:3]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:12]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 7761Diethyl MalonateHCID 3298032-(6-Chlorohexyloxy)tetrahydro-2H-pyranHCID 5360545Sodium

Produkt 1

HCID 99976152-[6-(Tetrahydro-pyran-2-yloxy)-hexyl]-malonic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Sodium (1.13 g, 49 mmol) in small quantities was dissolved in dry ethanol (100 ml) with constant stirring under a blanket of dry nitrogen. Diethyl malonate (8.0 g, 50 mmol) was added in one portion and the solution heated at 60° C. for 1 hour. 2-(6-Chloro-hexyloxy)-tetrahydropyran (9.3 g, 42.2 mmol) was added in one portion and the temperature raised to 75-80° C. and maintained at this level for 24 hours. After cooling, the inorganic solid was removed by filtration and solvent evaporated from the filtrate. The residue was dissolved in CH2Cl2 (50 ml), extracted with water (30 ml×2), dried (MgSO4) filtered and volatiles removed to leave a pale yellow oil. This oil was subject to chromatography on silica gel using pet ether 40:60/ether (200:40) as the eluent. The required product eluted with an rf=0.15 and was isolated as a colourless oil. Yield 8.7 g, (60%).

Aufarbeitung

  1. temperaturethe temperature raised to 75-80° C.
  2. temperaturemaintained at this level for 24 hours
  3. temperatureAfter cooling
  4. customthe inorganic solid was removed by filtration and solvent
  5. customevaporated from the filtrate
  6. dissolutionThe residue was dissolved in CH2Cl2 (50 ml)
  7. extractionextracted with water (30 ml×2)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customvolatiles removed
  11. customto leave a pale yellow oil
  12. washThe required product eluted with an rf=0.15
  13. customwas isolated as a colourless oil

Quellen und Nachweise

ORD-Eintrag
ord-ff87f7792e504deeb53719a718bd290c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767796B2

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