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

HRID 1453801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1453801
[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]

Komponenten

4

Edukt 2

HCID 7904Vinyl AcetateHCID 57528604HCID 57528604, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ca5a3222dadc434bb64cc7df8a7e0e49
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476684B2

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