Vinyl Acetate → (R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate

HRID 1803634Notes

Reaction equation

HRID 1803634 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[CH:3]1.[C:17](OC=C)(=[O:19])[CH3:18]>CC(CC(C)C)=O>[C:17]([O:1][C@@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[CH:3]1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 711700384-Hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone

Product 1

HCID 71170032(R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

4-Hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone (9 g, 41.26 mmol) was dissolved in isobutyl methyl ketone (90 mL), and vinyl acetate (8.4 g, 97.57 mmol) and Lipase derived from Alcaligenese spp. (0.9 g) were added to the solution, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered to remove Lipase and the filtrate was evaporated. The resulting residue was purified by chromatography on a silica gel column using hexane-EtOAc as eluent to give (R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate as yellow oil: 4.29 g (95% ee by HPLC using a chiral column) and (S)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone as yellow oil: 4.05 g (100% ee by HPLC using a chiral column)

Workup

  1. addition(0.9 g) were added to the solution
  2. filtrationThe reaction mixture was filtered
  3. customto remove Lipase
  4. customthe filtrate was evaporated
  5. customThe resulting residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-7a7055bfdc3643848fa0333f0a44ce1f
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

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