Water → Diethyl 2-benzyloxymethyl-2-cyclohexylmalonate

HRID 1197319

Reaktionsgleichung

Reaktionsgleichung von HRID 1197319
[CH:1]1([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>O1CCCC1>[CH2:23]([O:22][CH2:21][C:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 240541Diethyl 2-cyclohexylmalonate

Produkt 1

HCID 19373401Diethyl 2-benzyloxymethyl-2-cyclohexylmalonateAusbeute 107,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Diethyl cyclohexylmalonate (18.7 g) (ref. Beilstein 9, 739) was added to a stirred suspension of sodium hydride (4.8 g, 50% dispersion in oil) in dry tetrahydrofuran (50 ml) under nitrogen. The mixture was refluxed, with stirring, for one hour. The mixture was cooled and benzyl chloromethyl ether (13.9 g.) (Sigma Chemical Company) in dry tetrahydrofuran (50 ml) was added and the mixture was refluxed, with stirring, for three hours. The mixture was cooled and poured into water. The aqueous mixture was extracted with ether. The ether extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. Diethyl 2-benzyloxymethyl-2-cyclohexylmalonate (30 g.) was obtained as a brown oil and was used without further purification.

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. temperatureThe mixture was cooled
  3. temperaturethe mixture was refluxed
  4. stirringwith stirring, for three hours
  5. temperatureThe mixture was cooled
  6. extractionThe aqueous mixture was extracted with ether
  7. washThe ether extracts were washed with water
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7a6eec8ec7d04a5ba9536637ef3c5cc1
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116862

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