Carbon Dioxide → [5-(4-chlorophenyl)pyridin-2-yl]propynoic Acid

HRID 735058Notes

Reaction equation

HRID 735058 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[CH:20])=[N:17][CH:18]=2)=[CH:9][CH:8]=1.[C:21](=[O:23])=[O:22].C(OCC)(=O)C>C1COCC1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]([OH:23])=[O:22])=[N:17][CH:18]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8857Ethyl AcetateHCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridineHCID 178418339Butyllithium

Product 1

HCID 68816808[5-(4-chlorophenyl)pyridin-2-yl]propynoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-8 °C

Procedure

1.6 mL (2.46 mmol) of butyllithium solution (1.6M in hexane) are added dropwise at −10° C. to a solution of 0.5 g (2.34 mmol) of 5-(4-chlorophenyl)-2-ethynylpyridine in 30 mL of absolute THF and the mixture is stirred for five minutes at −8° C. stirred. The reaction mixture is combined with dry ice batchwise at −70° C., stirred for 1 hour at ambient temperature, and evaporated down. The residue is suspended in 5 mL of water and combined with 1.6 mL of 1N hydrochloric acid, whereupon a precipitate is formed. Then ethyl acetate is added and the suspension is filtered. The solid is dried in the vacuum drying chamber at 70° C. Yield: 0.25 g (41.5% of theory); melting point: 210° C.; C14H8ClNO2 (M=257.67); calc.: molecular ion peak (M+H)+: 258/260; found: molecular ion peak (M+H)+: 258/260.

Workup

  1. stirringstirred
  2. stirringstirred for 1 hour at ambient temperature
  3. customevaporated down
  4. customis formed
  5. filtrationthe suspension is filtered
  6. customThe solid is dried in the vacuum
  7. customdrying chamber at 70° C

Sources & evidence

ORD record
ord-55b272cce88845e2af6a75756e3d5100
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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