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

HRID 1803634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803634
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

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)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7a7055bfdc3643848fa0333f0a44ce1f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08350090B1

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