Hydrochloric Acid → 4,5-Dihydroxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole

HRID 1741965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741965
CC1(C)[O:17][CH:5]2[CH:6]([O:13][CH2:14][O:15][CH3:16])[CH2:7][C:8]3[CH:9]([CH2:10][O:11][N:12]=3)[CH:4]2[O:3]1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)C>[OH:3][CH:4]1[CH:9]2[CH2:10][O:11][N:12]=[C:8]2[CH2:7][CH:6]([O:13][CH2:14][O:15][CH3:16])[CH:5]1[OH:17]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 677933994,5-(Dimethylmethylenedioxy)-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole

Produkt 1

HCID 677918454,5-Dihydroxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazoleAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4,5-(Dimethylmethylenedioxy)-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole (257 mg) was dissolved in 10 ml of tetrahydrofuran, and 1 ml of 1N hydrochloric acid was added, followed by stirring the mixture at room temperature for 4 hours. The reaction mixture was diluted with diethyl ether, and neutralized with a sodium hydrogen carbonate aqueous solution. The organic layer was washed with a sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to afford 167 mg of 4,5-dihydroxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole having the following property (yield 77%).

Aufarbeitung

  1. washThe organic layer was washed with a sodium chloride aqueous solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c41e679ffc3740db915f7471708dcc03
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05334740

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