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

HRID 8215

Reaction equation

HRID 8215 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-387ee0643a204a82b0a724a86cb806fb
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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