Acetic Acid → 2-(4-Chlorophenyl)-3-cyclopropyl-3-oxopropanenitrile

HRID 872118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872118
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].C([O:15][C:16]([CH:18]1[CH2:20][CH2:19]1)=O)C.C(O)(=O)C>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:15])[C:9]#[N:10])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 78351Ethyl cyclopropanecarboxylateHCID 2415824-Chlorobenzyl cyanide

Produkt 1

HCID 145579492-(4-Chlorophenyl)-3-cyclopropyl-3-oxopropanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(4-Chlorophenyl)acetonitrile (5.74 g) is dissolved in 120 mL of THF at 0° C. After adding 60% NaH (4.2 g, 2.7 eq), the reaction mixture is stirred for 10 minutes. Ethylcyclopropane carboxylate is added and the mixture is stirred overnight. The reaction is stopped by adding acetic acid (5 mL) and water. The aqueous layer is extracted with ethyl acetate (50 mL×3). The collected organic layer is washed with brine and dehydrated with MgSO4. The dehydrated organic layer is concentrated by distillation under reduced pressure and purified by column chromatography to yield 7.74 g of the target compound. 1H NMR (CDCl3, 300 MHz): δ 7.42 (d, J=8.7 Hz, 2H), 7.34 (d, J=8.7 Hz, 2H), 4.79 (s, 1H), 2.10 (m, 1H) 1.16 (m, 2H), 1.03 (m, 2H).

Aufarbeitung

  1. stirringthe mixture is stirred overnight
  2. extractionThe aqueous layer is extracted with ethyl acetate (50 mL×3)
  3. washThe collected organic layer is washed with brine
  4. concentrationThe dehydrated organic layer is concentrated by distillation under reduced pressure
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cc149bc81b8f42e489ff98917477c86a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975264B2

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