Propionitrile → 4-(2-Cyanopropanoyl)benzonitrile

HRID 1517202

Reaktionsgleichung

Reaktionsgleichung von HRID 1517202
CC(C)([O-])C.[K+].[C:7](#[N:10])[CH2:8][CH3:9].CO[C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=1>O1CCCC1>[C:7]([CH:8]([CH3:9])[C:13]([C:14]1[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=1)=[O:22])#[N:10]

Komponenten

5

Edukt 3

HCID 7854PropionitrileHCID 70791Methyl 4-cyanobenzoateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 595047914-(2-Cyanopropanoyl)benzonitrileAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Potassium-tert-butoxide (7.76 g, 69.2 mmol) and propionitrile (4.84 mL, 69.2 mmol) was added to a solution of 4-cyano-benzoic acid methyl ester (11.15 g, 69.2 mmol) in tetrahydrofuran (100 mL). This mixture was stirred at room temperature for 16 hours, and then quenched onto an aqueous 10% solution (weight/volume) citric acid (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over magnesium sulphate, filtered, and evaporated under reduced pressure. This crude residue was triturated with tert-butyl methyl ether to give the title compound as a solid (7.00 g, 55%). 1H NMR (400 MHz, CDCl3): δ 1.65 (d, 3H), 4.35 (m, 1H), 7.85 (d, 2H), 8.10 (d, 2H).

Aufarbeitung

  1. customquenched onto an aqueous 10% solution (weight/volume) citric acid (100 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic extracts were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThis crude residue was triturated with tert-butyl methyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3319b0a476fa463693d0a6d0e14a5c52
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232269B2

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