Vinyl Acetate → (S)-1-[4-(1-hydroxyethyl)-phenyl]-3,3-dimethylbutan-1-one

HRID 911704노트

반응식

HRID 911704 반응식
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1)[CH3:3].[C:17](OC=C)(=[O:19])[CH3:18]>C(OC(C)C)(C)C>[C:17]([O:1][C@@H:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1)[CH3:3])(=[O:19])[CH3:18].[OH:1][C@H:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1)[CH3:3]

참가 물질

5

반응물 2

HCID 7904Vinyl AcetateHCID 576565131-[4-(1-Hydroxyethyl)-phenyl]-3,3-dimethylbutan-1-one

생성물 2

HCID 57655964(R)-1-(1-acetoxy-ethyl)-4-(3,3-dimethyl-butyryl)-benzene수율 36%HCID 57656522(S)-1-[4-(1-hydroxyethyl)-phenyl]-3,3-dimethylbutan-1-one수율 49%

시약·촉매·용매 1

HCID 7914Diisopropyl Ether용매

실험 절차

Dissolve 1-[4-(1-hydroxyethyl)-phenyl]-3,3-dimethylbutan-1-one (1.519 g, 6.905 mmol) in diisopropyl ether (20 mL). Add 4 Å molecular sieves powder (1.5 g), vinyl acetate (2 mL) and lipase Candida Antarctica acrylic resin (150 mg). Stir the mixture at room temperature overnight. Remove the solid residue by filtration. Concentrate the filtrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1) to give (R)-1-(1-acetoxy-ethyl)-4-(3,3-dimethyl-butyryl)-benzene as colorless oil (0.661 g, 36%) and (S)-1-[4-(1-hydroxyethyl)-phenyl]-3,3-dimethylbutan-1-one as a light yellow oil (0.737 g, 49%).

후처리

  1. customRemove the solid residue
  2. filtrationby filtration
  3. concentrationConcentrate the filtrate in vacuo
  4. custompurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1)

출처 및 근거

ORD 기록
ord-c48a9c3e42d94c32b2685e34eb983f4c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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