Carbon Dioxide → 3-(Pyridin-2-yl)propiolic acid

HRID 735081Notes

Reaction equation

HRID 735081 reaction equation
C([Li])CCC.[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)#[CH:7].[C:14](=[O:16])=[O:15]>C1COCC1>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]#[C:7][C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 137268EthynylpyridineHCID 178418339Butyllithium

Product 1

HCID 454898773-(Pyridin-2-yl)propiolic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.3 mL of n-butyllithium solution (1.6M in hexane) is added dropwise at −10° C. to a solution of 1 g (9.7 mmol) of 2-ethynylpyridine in 30 mL of absolute THF and stirred for 30 minutes. At −78° C., dry ice is added batchwise and the reaction mixture is allowed to heat up to ambient temperature. After about 1 hour, the reaction mixture is evaporated down and the residue is taken up in 10 mL of 1N hydrochloric acid while cooling with ice. The precipitate is filtered off, rinsed with isopropanol and diethyl ether, and dried in the vacuum drying chamber at 70° C. Yield: 0.6 g (42% of theory); melting point: 130° C.; C8H5NO2 (M=147.13); calc.: molecular ion peak (M+H)+: 148; found: molecular ion peak (M+H)+: 148.

Workup

  1. waitAfter about 1 hour
  2. customthe reaction mixture is evaporated down
  3. temperaturewhile cooling with ice
  4. filtrationThe precipitate is filtered off
  5. washrinsed with isopropanol and diethyl ether
  6. customdried in the vacuum
  7. customdrying chamber at 70° C

Sources & evidence

ORD record
ord-8556d2f2b90347478cb633882ac14035
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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