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m-Chloroperbenzoic acid → 4-(3-fluorophenyl)-2,2-dimethyl-5-(4-(methylsulfinyl)phenyl)furan-3(2H)-one

HRID 2298317
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2298317
[CH3:1][C:2]1([CH3:23])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[O:3]1.ClC1C=C(C=CC=1)C(OO)=[O:29].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][C:2]1([CH3:23])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:22])=[O:29])=[CH:17][CH:16]=2)[O:3]1
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Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 183855844-(3-Fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3(2H)-one

Produkt 1

HCID 183857244-(3-fluorophenyl)-2,2-dimethyl-5-(4-(methylsulfinyl)phenyl)furan-3(2H)-oneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a stirred solution of 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylthio)phenyl}-3(2H)-furanone (2.0 g, Example 166) in 50 ml dichloromethane, was added 1.5 g of m-chloroperoxybenzoic acid at 0° C. The reaction solution was stirred at the same temperature for one and half hours, after which 30 ml 5% aqueous sodium bicarbonate was added and the solution was stirred for another 10 minutes. Then the reaction mixture was concentrated in vacuo, and the resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography (hexane/ethylacetate=1:1) to give 1.3 g of 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone. mp: 143-144° C. NMR: δ1.58 (s, 6H), 2.76(s, 3H), 7.26-7.08 (m, 3H), 7.30-7.38 (m, 1H), 7.65 (d, J=8.2 Hz, 2H), 7.80 (d, J=8.2 Hz, 2H).

Aufarbeitung

  1. stirringthe solution was stirred for another 10 minutes
  2. concentrationThen the reaction mixture was concentrated in vacuo
  3. extractionthe resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customwas purified by column chromatography (hexane/ethylacetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-44e221cb971b43b89b8c75788e542981
Quelldatensatz
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06492416B1

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