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

HRID 1803638Notes

Reaction equation

HRID 1803638 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][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)=[CH:3]1.[C:23](OC=C)(=[O:25])[CH3:24]>CC(CC(C)C)=O>[C:23]([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][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)=[CH:3]1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 711700344-Hydroxy-2-(3-benzyloxybenzyl)cyclopent-2-enone

Product 1

HCID 71170042(R)-3-(3-benzyloxybenzyl)-4-oxocyclopent-2-enyl acetateYield 38%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

4-Hydroxy-2-(3-Benzyloxybenzyl)cyclopent-2-enone (5.73 g, 19.48 mmol) was dissolved in isobutyl methyl ketone (60 mL), and vinyl acetate (11.2 g, 13.01 mmol) and Lipase derived from Alculigenese spp (0.6 g) was added to the solution, and the mixture was stirred at room temperature for 1 day. 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 the (R)-3-(3-benzyloxybenzyl)-4-oxocyclopent-2-enyl acetate as yellow oil: 2.51 g (yield: 38%, 96% ee by HPLC using a chiral column) and (S)-4-hydroxy-2-(3-(benzyloxy)benzyl)cyclopent-2-enone as yellow oil: 2.68 g (yield: 47%, >99% ee by HPLC using a chiral column)

Workup

  1. additionwas 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-d8200ca31ac44ed3ab947ce1f051ac85
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

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