Vinyl Acetate → (1R)-1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]ethyl acetate

HRID 639836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639836
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]([OH:15])[CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:16](OC=C)(=[O:18])[CH3:17].C(CC([O-])=O)=C>C1(C)C=CC=CC=1>[C:16]([O:15][C@@H:13]([C:10]1[N:11]=[N:12][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:9]=1)[CH3:14])(=[O:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 7904Vinyl AcetateHCID 69710893-Butenoic acid, ion(1-)3×HCID 594242172-(3-chloro-phenyl)-2H-tetrazol-5-yl-ethanol

Produkt 1

HCID 59424210(1R)-1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]ethyl acetateAusbeute 400,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

2.22 g (9.93 mmol) racemic 1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]ethanol and 0.40 g Novozyme 435® are taken up under Ar in toluene (120 mL). After addition of 109 μL (1.18 mmol) vinyl acetate the reaction was run at r.t. o.n., followed by addition of 0.12 g Novozyme 435® and 218 μL (2.36 mmol) vinylacetate and increasing the temperature to 30° C. o.n. Further addition of 2 g Novozyme 435® and 150 μL (1.63 mmol) vinylacetate gave after 7 h ca 41% conversion of starting material. To enhance yield, the reaction was filtered over celite washed with DCM, evaporated to dryness, then taken up in toluene (250 mL). After addition of 0.3 g Novozyme 435® and 200 μL (2.17 mmol) vinylacetate under Ar, 48% conversion after 4 h at r.t. were achieved. Filtration over celite and washing with DCM gave crude which was purified over silica using DCM neat, followed by EA/Hep=1/2, yielding 1.26 g (48%) of the title compound. 1H NMR: 8.15 (m, 1H), 8.03 (m, 1H), 7.48 (m, 2H), 6.27 (q, 1H), 2.14 (s, 3H), 1.77 (d, 3H).

Aufarbeitung

  1. customwas run at r.t.
  2. customgave after 7 h ca 41% conversion of starting material
  3. customTo enhance yield
  4. filtrationthe reaction was filtered
  5. washover celite washed with DCM
  6. customevaporated to dryness
  7. filtrationFiltration over celite
  8. washwashing with DCM
  9. customgave crude which
  10. customwas purified over silica

Quellen und Nachweise

ORD-Eintrag
ord-c0e8498c0e2843bea78a3cb3a4256c7e
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691892B2

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