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Methyl iodide → methyl (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylate

HRID 849614
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 849614
CI.N12CCCN=C1CCCC[CH2:4]2.[CH3:14][C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[C:16]1[C:22]([OH:24])=[O:23]>CC(C)=O>[CH3:14][C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[C:16]1[C:22]([O:24][CH3:4])=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20647081(RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylic acid

Produkt 1

HCID 20647083methyl (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylateAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

0.88 cm3 (14 mmol) of methyl iodide and 1.8 cm3 (12 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, dropwise, were successively added to a solution of 2.3 g (10 mmol) of (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylic acid in 20 cm3 of acetone. The reaction mixture was subsequently heated at reflux for two hours. The acetone was subsequently concentrated, the residue was then stirred with 100 cm3 of water and then extracted with three times 30 cm3 of ethyl acetate. After drying over magnesium sulphate and concentrating under reduced pressure, 2.3 g (94%) of methyl (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylate were obtained in the form of an orange oil, the characteristic of which was as follows:

Aufarbeitung

  1. temperatureThe reaction mixture was subsequently heated
  2. temperatureat reflux for two hours
  3. concentrationThe acetone was subsequently concentrated
  4. extractionextracted with three times 30 cm3 of ethyl acetate
  5. dry with materialAfter drying over magnesium sulphate
  6. concentrationconcentrating under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e22cebf3e734468bab1519fd7930cdd
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06013662

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