Diethyl Malonate → 1,3-Diethyl 2-(3-oxocyclohexyl)propanedioate

HRID 523279

Reaktionsgleichung

Reaktionsgleichung von HRID 523279
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:8]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].N12CCCN=C1CCCCC2.CCOC(C)=O>C1COCC1>[O:7]=[C:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8]([O:16][CH2:17][CH3:18])=[O:15])[CH2:2]1

Komponenten

6

Edukt 4

HCID 7761Diethyl MalonateHCID 8857Ethyl AcetateHCID 135942-Cyclohexen-1-oneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 3170491,3-Diethyl 2-(3-oxocyclohexyl)propanedioateAusbeute 104 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of cyclohex-2-enone (3.05 mL, 30 mmol) and diethyl malonate (4.58 mL, 30.0 mmol) in THF (30 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (4.52 mL, 30.0 mmol) and heated at 50° C. for 16 h. The cooled mixture was poured into EtOAc and washed sequentially with 1M aqueous HCl and brine. The combined aqueous layers were extracted with EtOAc, and the combined organic phases were dried and concentrated to give diethyl 2-(3-oxocyclohexyl)malonate as an oil (8.0 g), used without further purification. Mass spectrum m/z 257 (M+H)+.

Aufarbeitung

  1. washwashed sequentially with 1M aqueous HCl and brine
  2. extractionThe combined aqueous layers were extracted with EtOAc
  3. customthe combined organic phases were dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a2ea0672ee5743b9ad4173f2ddb94550
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334290B2

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