Potassium Hydroxide → 5-(Carboxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydrocyclopenta[c]thiophene

HRID 375564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 375564
[C:1]([C:5]1([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:12][C:8]2=[CH:9][S:10][CH:11]=[C:7]2[CH2:6]1)([O:3]C)=[O:2].[OH-].[K+]>C(O)C.O.O1CCCC1>[C:1]([C:5]1([S:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:12][C:8]2=[CH:9][S:10][CH:11]=[C:7]2[CH2:6]1)([OH:3])=[O:2]

Komponenten

6

Edukt 2

HCID 14797Potassium HydroxideHCID 158144155-(Carbomethoxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene

Produkt 1

HCID 158144165-(Carboxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydrocyclopenta[c]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve 5-(carbomethoxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro- cyclopenta[c]thiophene (1.14 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate the aqueous phase and acidify with cold concentrated hydrochloric acid. Extract with methylene chloride (7 5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give 5-(carboxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydrocyclopenta[c]thiophene.

Aufarbeitung

  1. filtrationFilter
  2. customevaporate the solvent in vacuo
  3. customPartition between water (125 mL) and ether (75 mL)
  4. customSeparate the aqueous phase
  5. extractionExtract with methylene chloride (7 5 mL)
  6. dry with materialdry (Na2SO4)
  7. customevaporate the solvent in vacuo
  8. customPurify by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eba060cf26f1410fb3dd233193c6cd8f
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486513

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