Hydrochloric Acid → 5-[(4-Chlorophenyl)sulfanyl]-2-thiophenecarbaldehyde

HRID 467143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467143
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:21]=[O:22].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[S:10][C:11]([CH:21]=[O:22])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 27789892-[(4-Chlorophenyl)thio]thiopheneHCID 178418339Butyllithium

Produkt 1

HCID 70621945-[(4-Chlorophenyl)sulfanyl]-2-thiophenecarbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

To a solution of 2-(4-chlorophenylthio)thiophene (9.8 g) in dry tetrahydrofuran (75 ml) at -30° C. under nitrogen, was added dropwise, n-butyllithium (17.4 ml, 2.5M) and the solution left to stir at -30° C. for 2 hours. Dry dimethylformamide (5.1 ml) was then added and the solution allowed to stir at -30° C. for a further hour, warmed to room termperature and stirred overnight. The reaction mixture was poured onto 2N hydrochloric acid (75 ml), extracted with ether (2×100 ml), dried over MgSO4 and evaporated under reduced pressure to give a brown oil. The oil was flash chromatographed on a Sorbsil C60-40/60H column using 25% ether-hexane to give an orange oil.

Aufarbeitung

  1. stirringto stir at -30° C. for a further hour
  2. temperaturewarmed to room termperature
  3. stirringstirred overnight
  4. extractionextracted with ether (2×100 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customto give a brown oil
  8. customchromatographed on a Sorbsil
  9. customto give an orange oil

Quellen und Nachweise

ORD-Eintrag
ord-63649b4c93d64b28b120b21558b8520d
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158971

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