Potassium hydroxide methanol → (R)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone

HRID 1803641Notes

Reaction equation

HRID 1803641 reaction equation
C([O:4][C@@H:5]1[CH2:9][C:8](=[O:10])[C:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[CH:6]1)(=O)C.[OH-].[K+].CO>CO>[OH:4][C@@H:5]1[CH2:9][C:8](=[O:10])[C:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[CH:6]1

Participants

4

Reactant 2

HCID 23689386Potassium hydroxide methanolHCID 71170032(R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate

Product 1

HCID 71170057(R)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enoneYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3-(3-Methoxybenzyl)-4-oxocyclopent-2-enyl acetate (0.5 g, 1.48 mmol), was dissolved in MeOH (5 ml), 7% KOH/CH3OH (5 ml) was added to the solution, and the mixture was stirred at room temperature overnight. The mixture was evaporated and the resulting residue was neutralized by HCl to pH=6.5, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and evaporated. The resulting residue was purified by chromatography on a silica gel column using hexane-EtOAc as eluent to give (R)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone as yellow oil: 0.4 g, (yield: 92%) [α]D20=+3.5˜5.7°

Workup

  1. customThe mixture was evaporated
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe resulting residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-964c0f00d61643f89de5586330d3f14b
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

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