Water → Ethyl 2-(4,4-dimethyl-2-cyclohexen-1-ylidene)acetate

HRID 397717

Reaktionsgleichung

Reaktionsgleichung von HRID 397717
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][C:18]1([CH3:25])[CH2:23][CH2:22][C:21](=O)[CH:20]=[CH:19]1.O>O1CCCC1>[CH3:17][C:18]1([CH3:25])[CH2:23][CH2:22][C:21](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:20]=[CH:19]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-

Produkt 1

HCID 53954530Ethyl 2-(4,4-dimethyl-2-cyclohexen-1-ylidene)acetateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (60% dispersion in oil, 2.2 g, 55 mmol) in tetrahydrofuran (100 ml) at 0° C. was added ethyl 2-(diethoxyphosphoryl)acetate (11.2 g, 50 mmol) over 30 min, and the mixture was stirred at room temperature for 1 h. To this was added 4,4-dimethyl-2-cyclohexene-1-one over 20 min and the reaction mixture was stirred for a further 1 h. Water (100 ml) was added and the mixture was extracted with ether (2×100 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a colourless oil (9.7 g, 100%).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for a further 1 h
  2. extractionthe mixture was extracted with ether (2×100 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0ffd96e046f24d81b30dca21d1f9a2bc
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610711B2

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