HCID 67945849, Verbindung → HCID 67945766, Verbindung

HRID 727946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 727946
[CH3:1][N:2]([CH3:15])[C:3]([CH:5]1[S:10][C:9]2[O:11][CH:12]=[CH:13][C:8]=2[C:7](=O)[CH2:6]1)=O>O1CCCC1>[CH3:15][N:2]([CH2:3][CH:5]1[S:10][C:9]2[O:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6]1)[CH3:1]

Komponenten

3

Edukt 1

HCID 67945849HCID 67945849, Verbindung

Produkt 1

HCID 67945766HCID 67945766, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring, refluxing solution of N,N-dimethyl-4-oxo-5,6-dihydro-4H-furano[2,3-b]thiopyran-6-carboxamide (7.1 g, 0.0314 mol) in tetrahydrofuran (150 ml) was added dropwise borane-dimethyl sulfide complex (9.4 ml, 0.014 mol). The reaction was then stirred at reflux for 3 hr. when 6NHCl (25 ml) was added slowly and the reaction was heated at reflux for a further 1/2 hr. Most of the tetrahydrofuran was removed in vacuo and the residue was diluted with 6N HCl (50 ml) and heated again for 1/2 hr. The reaction was cooled to room temperature and water (100 ml) was added. The reaction was extracted once with ether (50 ml) and then basified with 10N NaOH (75 ml). The product was extracted with ethyl acetate (4×50 ml portions). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the product.

Aufarbeitung

  1. additionwas added dropwise borane-dimethyl sulfide complex (9.4 ml, 0.014 mol)
  2. temperatureat reflux for 3 hr
  3. additionwhen 6NHCl (25 ml) was added slowly
  4. temperaturethe reaction was heated
  5. temperatureat reflux for a further 1/2 hr
  6. customMost of the tetrahydrofuran was removed in vacuo
  7. additionthe residue was diluted with 6N HCl (50 ml)
  8. temperatureheated again for 1/2 hr
  9. additionwater (100 ml) was added
  10. extractionThe reaction was extracted once with ether (50 ml)
  11. extractionThe product was extracted with ethyl acetate (4×50 ml portions)
  12. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-bfc69e4f29054474881a72a781450adf
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05045561

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