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

HRID 911704ノート

反応式

HRID 911704 の反応式
[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]

参加物

5

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 7914Diisopropyl Ether溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c48a9c3e42d94c32b2685e34eb983f4c
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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