Water → Ethyl 1-cyanocyclopropanecarboxylate

HRID 512131

Reaktionsgleichung

Reaktionsgleichung von HRID 512131
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].Br[CH2:10][CH2:11]Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1([C:6]#[N:7])[CH2:11][CH2:10]1)=[O:8])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7764Ethyl cyanoacetateHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Produkt 1

HCID 380810Ethyl 1-cyanocyclopropanecarboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of cyano-acetic acid ethyl ester (11.3 g, 0.1 mol), 1,2-Dibromo-ethane, Na4(n-Bu)4Br and K2CO3 in DMF (100 mL) was heated to 80° C. overnight. The mixture was poured into water (600 mL) and extracted with EtOAc (3×50 mL). The combined organic layer was washed with brine, dried over Na2SO4, concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (petroleum ether: EtOAc=10:1˜5:1) to give 1-cyano-cyclopropanecarboxylic acid ethyl ester (10 g, yield: 72%). 1H NMR (CDCl3 400 MHz): δ4.21 (q, J=7.2 Hz, 2H), 1.65-1.61 (m, 2H), 1.58-1.55 (m, 2H), 1.28 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product, which
  6. customwas purified by column chromatography on silica gel (petroleum ether: EtOAc=10:1˜5:1)

Quellen und Nachweise

ORD-Eintrag
ord-501787d574114debbb6ecb65bb37e02b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102591B2

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