Sodium Hydroxide → (R)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone

HRID 1803636Notes

Reaction equation

HRID 1803636 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.OP([O-])(O)=O.[K+].OP(O)(O)=O.[OH-].[Na+]>>[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 3

HCID 14798Sodium HydroxideHCID 23690538Potassium phosphate (KH5(PO4)2)HCID 71170032(R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate2×

Product 1

HCID 71170057(R)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enoneYield 70%

Procedure

(R)-3-(3-Methoxybenzyl)-4-oxocyclopent-2-enyl acetate (0.1 g, 0.38 mmol) was added to KH2PO4—H3PO4 buffer (1 ml). The mixture was added thereto Lipase derived from Pseudomonas cepacia, and 1N NaOH was slowly added to the solution at room temperature to keep the pH=7˜7.5. After 3 hours, about 10% of (R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate remained. The reaction mixture was filtered to remove Lipase and the filtrate was extracted with EtOAc, 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: 58 mg (yield: 70%, >99.5% ee by HPLC using a chiral column)

Workup

  1. additionThe mixture was added
  2. additionwas slowly added to the solution at room temperature
  3. filtrationThe reaction mixture was filtered
  4. customto remove Lipase
  5. extractionthe filtrate was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe resulting residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-91de5c71c81e42229c8d3464dcbe0f02
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

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