Ethyl chloroformate → (6-Methyl-pyridin-2-yl)-propynoic acid ethyl ester

HRID 8215

Reaktionsgleichung

Reaktionsgleichung von HRID 8215
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1)#[CH:2].[Li+].CCC[CH2-].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>O1CCCC1>[CH2:19]([O:18][C:16](=[O:17])[C:2]#[C:1][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1)[CH3:20]

Komponenten

5

Edukt 3

HCID 10928Ethyl chloroformateHCID 61028n-Butyl lithiumHCID 134006352-Ethynyl-6-methylpyridine

Produkt 1

HCID 59700610(6-Methyl-pyridin-2-yl)-propynoic acid ethyl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-ethynyl-6-methyl-pyridine (0.5 g, 4.3 mmol) in tetrahydrofuran (20 mL) is cooled to −78° C. and treated with 1.6 M N-butyllithium in hexanes (2.9 mL, 4.7 mmol) and stirred for 0.5 h. This solution is then treated with ethyl chloroformate (2.85 mL, 30 mmol) and stirred for 3 h while the solution warms to room temperature. The reaction is quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The solvent is removed to yield 0.67 g (83%) of desired product as a light yellow oil.

Aufarbeitung

  1. stirringstirred for 3 h while the solution
  2. customwarms to room temperature
  3. customThe reaction is quenched with saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. customThe solvent is removed

Quellen und Nachweise

ORD-Eintrag
ord-387ee0643a204a82b0a724a86cb806fb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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