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Methyl Thioglycolate → methyl 6-benzyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate

HRID 505824
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 505824
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([CH:19]=O)=[C:9]1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][CH3:27])(=[O:25])[CH2:23][SH:24].CC(C)([O-])C.[K+]>C1COCC1>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]2[CH:19]=[C:23]([C:22]([O:26][CH3:27])=[O:25])[S:24][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 16907Methyl ThioglycolateHCID 23665647Potassium tert-butoxideHCID 860376661-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carbaldehyde

Produkt 1

HCID 68471240methyl 6-benzyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution (1.1 M) of 1-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carbaldehyde in THF at 0° C. was treated with methyl thioglycolate (1.5 eq.) and a solution (2 M) of potassium tert-butoxide (2.5 eq.) in THF. The mixture was stirred at 0° C. for 2 h then at RT for 40 h. The reaction was quenched with water and pH was turned to neutral value by addition of aqueous ammonium chloride (saturated solution). The mixture was extracted with AcOEt and the combined organic phase was washed with brine and dried. Evaporation of the solvent gave a residue that was purified by flash chromatography on silica gel (1:30 acetone/toluene) to afford the title compound (38%) as a solid.

Aufarbeitung

  1. waitat RT for 40 h
  2. customThe reaction was quenched with water and pH
  3. additionwas turned to neutral value by addition of aqueous ammonium chloride (saturated solution)
  4. extractionThe mixture was extracted with AcOEt
  5. washthe combined organic phase was washed with brine
  6. customdried
  7. customEvaporation of the solvent
  8. customgave a residue that
  9. customwas purified by flash chromatography on silica gel (1:30 acetone/toluene)

Quellen und Nachweise

ORD-Eintrag
ord-dceaec4639154039b363ea0e4b093a20
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781431B2

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