(Triphenylphosphoranylidene)acetonitrile → (E)-Methyl 4,5-dichloro-2-(2-cyanovinyl)benzoate

HRID 715997

Reaktionsgleichung

Reaktionsgleichung von HRID 715997
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH:13]=O)[CH:3]=1.C1(P(=[CH:34][C:35]#[N:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](/[CH:13]=[CH:34]/[C:35]#[N:36])[CH:3]=1

Komponenten

4

Edukt 2

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 86647797Methyl 4,5-dichloro-2-formylbenzoate

Produkt 1

HCID 86647796(E)-Methyl 4,5-dichloro-2-(2-cyanovinyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of the product from Example 56C (2.0 g, 8.6 mmol) and (triphenylphosphoranylidene)acetonitrile (2.87 g, 9.5 mmol) in toluene (30 mL) was refluxed for 24 hours. The reaction was cooled to room temperature and filtered through a short plug of silica gel eluting with diethyl ether to remove the triphenyl phosphine oxide. The filtrate was concentrated and the residue was purified via flash chromatography on a silica gel:column (5:95 ethyl acetate:hexane) to afford the title compound and the corresponding Z isomer. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.88 (s, 3H) 6.55 (d, J=16.27 Hz, 1H) 8.05 (d, J=16.95 Hz, 1H) 8.09 (s, 1H) 8.13 (s, 1H); MS (DCI+) m/z 273.0 [M+H]+.

Aufarbeitung

  1. temperaturewas refluxed for 24 hours
  2. filtrationfiltered through a short plug of silica gel eluting with diethyl ether
  3. customto remove the triphenyl phosphine oxide
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified via flash chromatography on a silica gel

Quellen und Nachweise

ORD-Eintrag
ord-13a5e6b49ab040bd9fbfb79bae8bcdbe
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187483B2

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