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

HRID 2071023노트

반응식

HRID 2071023 반응식
[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]

참가 물질

5

반응물 2

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

생성물 2

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5f0992afda0a4570b99e91d2630d0851
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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