Phosphoric Acid → methyl 6-cyclohex-1-en-1-yl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505778
[C:1]1([C:7]2[NH:11][C:10]3[CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[S:14][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC(=O)C)(=O)C.[C:26]1(=O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.P(=O)(O)(O)O>C(O)(=O)C>[C:26]1([C:8]2[C:9]3[S:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:10]=3[NH:11][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 7967CyclohexanoneHCID 11492603methyl 5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Produkt 1

HCID 11559121methyl 6-cyclohex-1-en-1-yl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution (0.2 M) of methyl 5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in acetic acid was treated with acetic anhydride (10 eq.), cyclohexanone (10 eq.) and 85% phosphoric acid (2.3 eq.). The mixture was heated at 80° C. for 3 h, then was poured into ice cold ammonium hydroxide. The product was extracted with AcOEt and the combined organic layers were washed sequentially with aqueous HCl (1 N), aqueous NaHCO3 (saturated solution) and brine then dried and concentrated. The crude was purified by flash chromatography on silica gel (1:4 AcOEt/petroleum ether) affording the title compound (69%) as a solid.

Aufarbeitung

  1. additionwas poured into ice cold ammonium hydroxide
  2. extractionThe product was extracted with AcOEt
  3. washthe combined organic layers were washed sequentially with aqueous HCl (1 N), aqueous NaHCO3 (saturated solution) and brine
  4. customthen dried
  5. concentrationconcentrated
  6. customThe crude was purified by flash chromatography on silica gel (1:4 AcOEt/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-50908046b11849b491fd4af700b48971
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781431B2

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