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

HRID 911704Notes

Reaction equation

HRID 911704 reaction equation
[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]

Participants

5

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-c48a9c3e42d94c32b2685e34eb983f4c
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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