Dihydrobenzofuran → 2,3-Dihydrobenzofuran-5-sulfonyl Chloride

HRID 1081346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081346
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7]1>CN(C)C=O>[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:14][C:9]=2[CH2:8][CH2:7]1

Komponenten

4

Edukt 2

HCID 10329DihydrobenzofuranHCID 24648Sulfuryl chloride

Produkt 1

HCID 27761542,3-Dihydrobenzofuran-5-sulfonyl ChlorideAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To. 3.35 g of dimethylformamide, at 0° C. under an atmosphere of nitrogen, added 6.18 g of sulfuryl chloride. The mixture was stirred 15 min and treated with 4.69 g of 2,3-dihydrobenzofuran. The mixture was then heated at 100° C. for 1.5 h, cooled to about 40° C., poured onto ice, extracted with CH2Cl2, dried over MgSO4, filtered, and concentrated in vacuo. The residue was taken up in ethyl acetate, cooled to 5° C. for 16 h, and the resultant pink crystals collected by vacuum filtration to provide 6.12 g of the title product. TLC: Rf=0.41, 10% ethyl acetate in hexane. (1H)-NMR (CDCl3) consistent with structure.

Aufarbeitung

  1. temperaturecooled to about 40° C.
  2. additionpoured onto ice
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. temperaturecooled to 5° C. for 16 h
  8. filtrationthe resultant pink crystals collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-1245a1770e6848599a9c8456a6318c18
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05585397

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