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m-Chloroperbenzoic acid → HCID 15280201, Verbindung

HRID 1492470
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1492470
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:20][CH2:21][C@@H:22]1[C@@H:27]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26][CH:25]=[CH:24][CH2:23]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S([O-])(O)=O.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.CCCCCC>[C:30]([O:29][CH2:28][C@@H:27]1[C@@H:22]([CH2:21][O:20][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:23][CH:24]2[CH:25]([O:9]2)[CH2:26]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
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Komponenten

7

Edukt 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10760318HCID 10760318, VerbindungHCID 23665763Sodium Bisulfite

Produkt 1

HCID 15280201HCID 15280201, VerbindungAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

m-Chloroperbenzoic acid (777 mg, 4.5 mmoles) was added to a solution of (4S,5S)-4,5-bis(benzoyloxymethyl)-1-cyclohexene (1.05 g, 3.0 mmoles) in methylene chloride (6 ml) under cooling with ice. After stirring the mixture at room temperature for 2 hours, a saturated aqueous solution of sodium hydrogen sulfite was added to the reaction mixture and the excessive peracid was decomposed, after which a saturated aqueous solution of sodium hydrogen carbonate was added and the whole mixture was subjected to extraction with ethyl ether. The ether extract solution was washed with water and then with saturated aqueous solution of sodium hydrogen carbonate, and dried on anhydrous sodium sulfate. After distilling off the solvent therefrom under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3, v/v) to obtain (3S,4S)-3,4-bis(benzoyloxymethyl)-7-oxabicyclo[4.1.0]heptane (1.025 g, Yield 93%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. extractionthe whole mixture was subjected to extraction with ethyl ether
  3. extractionThe ether extract solution
  4. washwas washed with water
  5. dry with materialwith saturated aqueous solution of sodium hydrogen carbonate, and dried on anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent
  7. customunder reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e2705e36c2b64bd8b4e56b3f93b05f71
Quelldatensatz
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05374625

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