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

HRID 22524Notes

Reaction equation

HRID 22524 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][O: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][O:10][CH:11]=[C:7]2[CH2:6]1)([OH:3])=[O:2]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 158144065-(Carbomethoxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro-cyclopenta[c]furan

Product 1

HCID 158144075-(Carboxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydrocyclopenta[c]furan

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 5-(carbomethoxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro-cyclopenta[c]furan (1.08 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 (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]furan.

Workup

  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 (75 mL)
  6. dry with materialdry (Na2SO4)
  7. customevaporate the solvent in vacuo
  8. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-00f4cd43d9e043459dbf554adba471f3
Source dataset
uspto-grants-1995_06
Patent number
US05428158

Reaction notes

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