Hydrochloric Acid → (R)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone

HRID 1803637Notes

Reaction equation

HRID 1803637 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.Cl>C1COCC1>[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 313Hydrochloric AcidHCID 71170032(R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate

Product 1

HCID 71170057(R)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enoneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-3-(3-Methoxybenzyl)-4-oxocyclopent-2-enyl acetate (0.1 g, 0.38 mmol) was dissolved in THF (1 ml), 3N HCl (5 ml) was added to the solution, and the mixture was stirred at room temperature overnight. The reaction was quenched with saturated NaHCO3 to pH=6.9 and extracted with EtOAc and 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 the (R)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone as yellow oil: 71 mg (yield: 85%)

Workup

  1. customThe reaction was quenched with saturated NaHCO3 to pH=6.9
  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-649434777df14c7d9a134450507ad1fc
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

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