Vinyl Acetate → (R)-1-(5-bromopyridin-3-yl)ethyl acetate

HRID 2071023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2071023
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.[C:11]([O:14][CH:15]=[CH2:16])(=[O:13])[CH3:12]>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.[C:11]([O:14][C@@H:15]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH3:16])(=[O:13])[CH3:12]

Komponenten

5

Edukt 2

HCID 7904Vinyl AcetateHCID 129974353-Bromo-5-(1-hydroxyethyl)pyridine

Produkt 2

HCID 68669858(R)-1-(5-bromopyridin-3-yl)ethyl acetateHCID 68671332(S)-1-(5-bromopyridin-3-yl)ethan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(5-bromopyridin-3-yl)ethanol (2.0 g) in anhydrous Et2O (50 mL) at 0° C., was vinyl acetate (2 mL), 4A° molecular sieves (2.0 g), Lipase immobilized from Candida Antarctica (200 mg) and the reaction was stirred for 16 h. The catalyst and molecular sieves were filtered off and the solvent was concentrated under reduced pressure. The residue was purified by column chromatography (30% EtOAc in hexanes) to provide 1.0 g of (S)-1-(5-bromopyridin-3-yl)ethanol and 1.18 g of (R)-1-(5-bromopyridin-3-yl)ethyl acetate.

Aufarbeitung

  1. customat 0° C.
  2. filtrationThe catalyst and molecular sieves were filtered off
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5f0992afda0a4570b99e91d2630d0851
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

Notizen zur Reaktion

Wird geladen…