Hydrochloric Acid → Ethyl 2-(3-methoxy-6,6-dimethyl-2-oxocyclohex-3-en-1-yl)-2-oxoacetate

HRID 875094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875094
[H-].[Na+].[CH3:3][O:4][C:5]1[C:6](=[O:13])[CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][CH:10]=1.[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>O1CCCC1.O>[CH3:3][O:4][C:5]1[C:6](=[O:13])[CH:7]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]([CH3:11])([CH3:12])[CH2:9][CH:10]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 552979862-Methoxy-5,5-dimethylcyclohex-2-enone

Produkt 1

HCID 57444091Ethyl 2-(3-methoxy-6,6-dimethyl-2-oxocyclohex-3-en-1-yl)-2-oxoacetateAusbeute 2.084,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

60% sodium hydride in mineral oil (2.41 g, 60.3 mmol) was suspended in anhydrous tetrahydrofuran (60 mL) under argon atmosphere and treated with a solution of 2-methoxy-5,5-dimethyl-cyclohex-2-enone (6.20 g, 40:2 mmol) in anhydrous tetrahydrofuran (50 mL). After 15 minutes, a solution of diethyl oxalate (8.17 mL, 60.3 mmol) in anhydrous tetrahydrofuran (50 mL) was added and the mixture was refluxed for 1 hour. The slurry was diluted with water (800 mL), acidified with 1 N HCl (50 mL) and extracted with ethyl acetate (500 mL×2). The organic layers were collected, washed with brine, dried on Na2SO4 and evaporated to dryness to obtain the crude title compound (10.60 g) as an orange oil, which was used without further purification.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hour
  2. extractionextracted with ethyl acetate (500 mL×2)
  3. customThe organic layers were collected
  4. washwashed with brine
  5. customdried on Na2SO4
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d877e6fcc0bc4809a37e9261ef81ec40
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981089B2

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