Maleic Anhydride → 2,4-Dioxo-6-phenylthio-3-oxabicyclo[3.2.0]heptane

HRID 465769

Reaktionsgleichung

Reaktionsgleichung von HRID 465769
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH:8]([S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH2:9].[Cl-].[Cl-].C([Al+2])C>ClCCCl.C(Cl)Cl>[O:5]=[C:4]1[O:6][C:1](=[O:7])[CH:2]2[CH:3]1[CH2:9][CH:8]2[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 7923Maleic AnhydrideHCID 74572Phenyl Vinyl SulfideHCID 16686341Ethyl aluminium dichloride

Produkt 1

HCID 197942712,4-Dioxo-6-phenylthio-3-oxabicyclo[3.2.0]heptaneAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of maleic anhydride (0.39 g, 4 mmol) and phenyl vinyl sulfide (0.52, 4 mmol) in 17 mL of 1,2-dichloroethane under nitrogen, was added 2 mL (0.5 equiv) of ethylaluminum dichloride. The resultant solution was stirred at ambient temperature for 0.5 h and then diluted with 75 mL of methylene chloride. The methylene chloride solution was washed three times with saturated aqueous ammonium chloride solution and once with brine, dried over anhydrous sodium sulfate and concentrated to give 0.85 g of the title compound; EI-MS, m/e (rel intensity): 234 (M+, 23), 136 (100), 109 (12), 91 (21).

Aufarbeitung

  1. washThe methylene chloride solution was washed three times with saturated aqueous ammonium chloride solution
  2. dry with materialonce with brine, dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4428d5b6560c4e069945e042110f6c04
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153352

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