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

HRID 505794
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 505794
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.[C:27]1(=O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.P(=O)(O)(O)O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:10]=3[C:9]=2[C:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=2)=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 7967CyclohexanoneHCID 24976015methyl 5-(4-chlorophenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Produkt 1

HCID 68467153methyl 5-(4-chlorophenyl)-6-cyclohex-1-en-1-yl-4H-thieno[3,2-b]pyrrole-2-carboxylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution (0.2 M) of methyl 5-(4-chlorophenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in acetic acid was treated with acetic anhydride (2.5 eq.), cyclohexanone (10 eq.) and 85% phosphoric acid (2.1 eq.). The mixture was heated at 80° C. for 3.5 days. After cooling down it 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 NaHCO, (saturated solution) and brine then dried and concentrated. The crude was purified by flash chromatography on silica gel (1:9 to 1:4 AcOEt/petroleum ether) affording the title compound (91%) as a solid.

Aufarbeitung

  1. temperatureAfter cooling down it
  2. additionwas poured into ice cold ammonium hydroxide
  3. extractionThe product was extracted with AcOEt
  4. washthe combined organic layers were washed sequentially with aqueous HCl (1 N), aqueous NaHCO, (saturated solution) and brine
  5. customthen dried
  6. concentrationconcentrated
  7. customThe crude was purified by flash chromatography on silica gel (1:9 to 1:4 AcOEt/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-a441f15e86f544f48defa17382110b55
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781431B2

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