Vinyl Acetate → (1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetate

HRID 500533Notes

Reaction equation

HRID 500533 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]([OH:15])[CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:16](OC=C)(=[O:18])[CH3:17]>C1(C)C=CC=CC=1>[C:16]([O:15][C@@H:13]([C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:12][N:11]=1)[CH3:14])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 57528604HCID 57528604, compound

Product 1

HCID 44605723(1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetateYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound of Example 7.1 (106.5 g, 476 mmol) and Novozyme 435® (13 g) are taken up under Ar in dry toluene (1.5 L). After addition of vinyl acetate (66 mL, 716 mmol) the reaction was run at RT over night, followed by filtration over diatomaceous earth and washing with DCM. The solvent was evaporated in vacuo and the crude product was subjected to column chromatography on silica using dichloromethane/methanol (20:1) to give the title compound (50 g, 47%).

Workup

  1. waitwas run at RT over night
  2. filtrationfollowed by filtration over diatomaceous earth
  3. washwashing with DCM
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-33bacb8dec87444bb34600ae5399f68c
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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