Hydrochloric Acid → 2-Methylene-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone

HRID 1741961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741961
O[CH2:2][CH:3]1[CH:8]2[O:9][C:10]([CH3:13])([CH3:12])[O:11][CH:7]2[CH:6]([O:14][CH2:15][O:16][CH3:17])[CH2:5][C:4]1=[O:18].CS(Cl)(=O)=O.Cl>N1C=CC=CC=1>[CH2:2]=[C:3]1[CH:8]2[O:9][C:10]([CH3:13])([CH3:12])[O:11][CH:7]2[CH:6]([O:14][CH2:15][O:16][CH3:17])[CH2:5][C:4]1=[O:18]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 190110002-Hydroxymethyl-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone

Produkt 1

HCID 190110072-Methylene-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanoneAusbeute 8,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Pyridine (0.5 ml) was added to 22 mg of 2-hydroxymethyl-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone, and 0.1 ml of methanesulfonyl chloride was then added at 0° C., followed by stirring the mixture for 2 hours. The reaction mixture was poured into cold dilute hydrochloric acid, and extracted with diethyl ether. The extract was washed with a saturated sodium hydrogen carbonate aqueous solution and then with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to provide 1.8 mg of 2-methylene-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone having the following properties (yield 8.8%).

Aufarbeitung

  1. additionwas then added at 0° C.
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with a saturated sodium hydrogen carbonate aqueous solution
  4. dry with materialwith a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-552880e9b5034f1990fb48fe014ef201
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05334740

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