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

HRID 1453801Notes

Reaction equation

HRID 1453801 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

1-[5-(3-chlorophenyl)isoxazol-3-yl]ethanol (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 r.t. over night, followed by filtration over celite 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%). 1H NMR: 7.76 (m, 1H), 7.65 (m, 1H), 7.41 (m, 2H), 6.54 (s, 1H), 6.07 (q, 1H), 2.13 (s, 3H), 1.66 (d, 3H). LC-MS (M++1)=266.

Workup

  1. waitwas run at r.t. over night
  2. filtrationfollowed by filtration over celite
  3. washwashing with DCM
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ca5a3222dadc434bb64cc7df8a7e0e49
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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