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

HRID 2396000Notes

Reaction equation

HRID 2396000 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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-tetrahydro-cyclopenta[c]thiophene.

Workup

  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

Sources & evidence

ORD record
ord-dc611656b11942f185f2fc89fe387e23
Source dataset
uspto-grants-1996_02
Patent number
US05491141

Reaction notes

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