Potassium Hydroxide → 1-(Carboxy)-1-(4-methoxybenzylthio)cyclopentane

HRID 260689Notes

Reaction equation

HRID 260689 reaction equation
[C:1]([C:5]1([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)([O:3]C)=[O:2].[OH-].[K+]>C(O)C.O.O1CCCC1>[C:1]([C:5]1([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)([OH:3])=[O:2]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 158143811-(Carbomethoxy)-1-(4-methoxybenzylthio)cyclopentane

Product 1

HCID 158143821-(Carboxy)-1-(4-methoxybenzylthio)cyclopentaneYield 72%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1-(carbomethoxy)-1-(4-methoxylbenzylthio)cyclopentane (3.3 mmol) in 95% ethanol (18 mL), water (9 mL), and tetrahydrofuran (10 mL). Treat with potassium hydroxide (0.91 g, 16 mmol). Stir at room temperature for 2 hours and evaporate the solvent in vacuo. Partition between water (50 mL) and ethyl ether (30 mL). Acidify the aqueous phase with cold concentrated hydrochloric acid and extract with methylene chloride (50 mL). Dry (MgSO4) and evaporate the solvent in vacuo to give 1-(carboxy)-1-(4-methoxybenzylthio)cyclopentane as a pale yellow oil (483 mg, 72%).

Workup

  1. customevaporate the solvent in vacuo
  2. customPartition between water (50 mL) and ethyl ether (30 mL)
  3. extractionextract with methylene chloride (50 mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-2c7a487324984758b3d284a7b1fe2e04
Source dataset
uspto-grants-1996_06
Patent number
US05529996

Reaction notes

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