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

HRID 2395982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2395982
[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 theaqueous phase and acidify with cold concentrated hydrochloric acid. Extractwith methylene chloride (75 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 theaqueous phase
  5. dry with materialExtractwith methylene chloride (75 mL), dry (Na2SO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-82bb1a4554274843b50c4a2009265f0c
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05491142

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