Potassium Hydroxide → 4H,5H,6H-cyclopenta[c]thiophene-5-carboxylic acid

HRID 375562Notes

Reaction equation

HRID 375562 reaction equation
[C:1]([CH:6]1[CH2:13][C:9]2=[CH:10][S:11][CH:12]=[C:8]2[CH2:7]1)([O:3]CC)=[O:2].[OH-].[K+]>C(O)C.O>[C:1]([CH:6]1[CH2:13][C:9]2=[CH:10][S:11][CH:12]=[C:8]2[CH2:7]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 158144125-(Carboethoxy)-2,4,5,6-tetrahydrocyclopenta[c]thiophene

Product 1

HCID 158144134H,5H,6H-cyclopenta[c]thiophene-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Dissolve 5,5-(dicarboethoxy)-2,4,5,6-tetrahydrocyclopenta[c]thiophene (16.2 g, 60.6 mmol) in dimethylsulfoxide (140 ml). Add water (14 mL) and lithium chloride (7.0 g, 0.16 mol). Heat at reflux for 4 hours, cool and partition between water (150 mL) and methylene chloride (2×150 mL). Wash the organic phase with water (150 mL), dry (MgSO4) and pass through a silica gel plug to give 5-(carboethoxy)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene. Dissolve 5-(carboethoxy)-2,4,5,6-tetrahydrocyclopenta[c]thiophene (6.68 g, 34.1 mmol) in ethanol (95%, 150 mL) and water (75 mL). Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for 1 hour. Partition between water (150 mL) and ethyl ether (2×150 mL). Acidify the aqueous phase with hydrochloric acid to pH 1. Extract with methylene chloride (2×150 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 5-(carboxy)- 2,4,5,6-tetrahydrocyclopenta[c]thiophene.

Workup

  1. customPartition between water (150 mL) and ethyl ether (2×150 mL)
  2. extractionExtract with methylene chloride (2×150 mL)
  3. dry with materialdry (Na2SO4)
  4. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-c782a187d27949e99e38dbd8135afa86
Source dataset
uspto-grants-1996_01
Patent number
US05486513

Reaction notes

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