m-Chloroperbenzoic acid → Methyl 6-oxabicyclo[3.1.0]hexane-1-carboxylate

HRID 1160606

Reaktionsgleichung

Reaktionsgleichung von HRID 1160606
[C:1]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4][CH2:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:18])C=1>ClCCl.CCOC(C)=O>[C:1]12([C:6]([O:8][CH3:9])=[O:7])[O:18][CH:5]1[CH2:4][CH2:3][CH2:2]2

Komponenten

5

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 549129Methyl cyclopent-1-ene-1-carboxylate

Produkt 1

HCID 14314662Methyl 6-oxabicyclo[3.1.0]hexane-1-carboxylateAusbeute 142 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl cyclopent-1-ene-1-carboxylate (30.0 g, 237.8 mmol) was dissolved in 20 mL of dichloromethane and 3-chloroperbenzoic acid (64.4 g, 373.3 mmol) was added. The reaction was allowed to stir vigorously for 2 hours. The reaction mixture was diluted with EtOAc and washed with 0.5 N NaOH. The organic layer was dried over sodium sulfate, filtered and concentrated to give 48.0 grams of methyl 6-oxabicyclo[3.1.0]hexane-1-carboxylate.

Aufarbeitung

  1. washwashed with 0.5 N NaOH
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-278d5332798f4b509f6d93817127053a
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816380B2

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