Ethanol → gamma-oxo-alpha-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoic acid

HRID 362469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362469
C(O)C.[O:4]=[C:5]([N:25]1[CH2:29][C:28]2=[CH:30][S:31][CH:32]=[C:27]2[CH2:26]1)[CH2:6][CH:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([O:10]CC1C=CC=CC=1)=[O:9].[OH-].[Na+]>O1CCCC1>[O:4]=[C:5]([N:25]1[CH2:26][C:27]2=[CH:32][S:31][CH:30]=[C:28]2[CH2:29]1)[CH2:6][CH:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([OH:10])=[O:9]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 15337444Phenylmethyl gamma-oxo-alpha-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoate

Produkt 1

HCID 15337447gamma-oxo-alpha-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoic acidAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

15 ml of ethanol are added to a solution of 1.22 g (3 mmol) of phenylmethyl γ-oxo-α-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoate in 15 ml of tetrahydrofuran, followed, at 0° C., by a solution of 0.36 g (9 mmol) of sodium hydroxide. After 1 h at room temperature, the medium is concentrated to about 15 ml, 15 ml of water are added and then the mixture is acidfied with 2N hydrochloric acid to pH 2 and extracted with three times 25 ml of ethyl acetate. The organic phases are pooled, washed with a saturated sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The residue is triturated with diethyl ether to give 0.71 g of a white solid.

Aufarbeitung

  1. concentrationthe medium is concentrated to about 15 ml, 15 ml of water
  2. additionare added
  3. extractionextracted with three times 25 ml of ethyl acetate
  4. washwashed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness
  7. customThe residue is triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-53f626051fca4b698e308dea03481728
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869518

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