Diethyl Ether → 2-Cyano-3-isopropyl-hexanoic acid methyl ester

HRID 1374224

Reaktionsgleichung

Reaktionsgleichung von HRID 1374224
[CH2:1]([Mg]Cl)[CH2:2][CH3:3].[CH3:6]COCC.[C:11]([C:13](=[CH:17][CH:18]([CH3:20])[CH3:19])[C:14]([OH:16])=[O:15])#[N:12]>C1COCC1>[CH3:6][O:15][C:14](=[O:16])[CH:13]([C:11]#[N:12])[CH:17]([CH:18]([CH3:20])[CH3:19])[CH2:1][CH2:2][CH3:3]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 2925472-Cyano-4-methylpent-2-enoic acidHCID 178455855HCID 178455855, Verbindung

Produkt 1

HCID 541521852-Cyano-3-isopropyl-hexanoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

A 2.0 M solution of propyl magnesium chloride in Et2O (9.8 mL, 19.6 mmol) is added to a solution of 2-cyano-4-methyl-2-pentenoic acid (3.0 g, 19.6 mmol) in 50 mL of THF which is cooled in an IPA/dry ice bath to −40° C. under argon. The solution is stirred for 4 hours, and the reaction is quenched by addition of 50 mL of saturated KH2PO4. The THF is evaporated, and the remaining oil is chromatographed under medium pressure over silica gel with 50% CH2Cl2/hexane. Yield=1.9 g (50%) of 2-cyano-3-isopropyl-hexanoic acid methyl ester as an oil.

Aufarbeitung

  1. customthe reaction is quenched by addition of 50 mL of saturated KH2PO4
  2. customThe THF is evaporated
  3. customthe remaining oil is chromatographed under medium pressure over silica gel with 50% CH2Cl2/hexane

Quellen und Nachweise

ORD-Eintrag
ord-eaf66287f5414635bb7b46e74b9a085e
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07164034B2

Verknüpfte Notizen

Wird geladen…