Potassium Carbonate → Pentyl 4-(3,4-dicyanophenoxy)benzoate

HRID 39207

Reaktionsgleichung

Reaktionsgleichung von HRID 39207
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[OH:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:22]([O:21][C:19]([C:18]1[CH:27]=[CH:28][C:15]([O:14][C:4]2[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=2)[C:8]#[N:9])=[CH:16][CH:17]=1)=[O:20])[CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 23019Pentyl 4-hydroxybenzoateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Produkt 1

HCID 68981262Pentyl 4-(3,4-dicyanophenoxy)benzoateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 4-nitrophthalonitrile (1.00 g, 7 mmol), pentyl 4-hydroxybenzoate (1.45 g, 7 mmol) and dried potassium carbonate (6.38 g, 46.2 mmol) in anhydrous DMF (50 mL) was stirred overnight at 85° C. under argon. After cooling to room temperature, the mixture was diluted with ethyl acetate (60 mL) and water (40 mL). The organic layer was separated, and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated solution of NaHCO3 (40 mL), brine (40 mL) and dried over anhydrous sodium sulfate. The solvents were removed in vacuo, and the crude product was purified by column chromatography on silica gel using a dichloromethane/acetonitrile mixture (20:1) as an eluent to give the product in 85% yield. [1H NMR (δ, ppm, CDCl3): 8.15 (d, 2H, J=8.7 Hz), 7.77 (d, 1H, J=8.7 Hz), 7.35 (d, 1H, J=2.3 Hz), 7.30 (d, 1H, J=8.7 Hz), 7.12 (d, 2H, J=8.7 Hz), 4.34 (2H, t, OCH2, J=6.7 Hz), 1.79 (m, 2H, CH2), 1.42 (m, 4H, CH2CH2), 0.94 (t, 3H, J=7 Hz, CH3).]

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers were washed with a saturated solution of NaHCO3 (40 mL), brine (40 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customthe crude product was purified by column chromatography on silica gel using a dichloromethane/acetonitrile mixture (20:1) as an eluent
  8. customto give the product in 85% yield

Quellen und Nachweise

ORD-Eintrag
ord-55bb5dca550f4cd6ac687da0cbf92ba2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524891B2

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