Sodium hydride → 5-(4-Ethoxycarbonylbuta-1,3-dienyl)imidazo[1,5-a]pyridine

HRID 280201Notes

Reaction equation

HRID 280201 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6](/[CH:8]=[CH:9]/[CH2:10]P(OCC)(OCC)=O)=[O:7].[CH:19]([C:21]1[N:26]2[CH:27]=[N:28][CH:29]=[C:25]2[CH:24]=[CH:23][CH:22]=1)=O>C1(C)C=CC=CC=1>[CH2:4]([O:5][C:6]([CH:8]=[CH:9][CH:10]=[CH:19][C:21]1[N:26]2[CH:27]=[N:28][CH:29]=[C:25]2[CH:24]=[CH:23][CH:22]=1)=[O:7])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 13206163Imidazo[1,5-a]pyridine-5-carbaldehyde

Product 1

HCID 539135015-(4-Ethoxycarbonylbuta-1,3-dienyl)imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of 150 mg of sodium hydride in 25 ml of toluene is added 550 mg of triethyl 4-phosphonocrotonate in a dropwise manner over a 10-minute period. The reaction mixture is maintained at 5° by cooling in an ice-water bath. On completion of the addition, 300 mg of 5-formylimidazol[1,5-a]pyridine is added to the reaction mixture which is then allowed to stir at room temperature for 1 hour. The reaction mixture is poured into 100 ml of ice water and extracted with 2×100 ml of ethyl acetate. The ethyl acetate extracts are combined and dried over magnesium sulfate, filtered and evaporated to dryness to yield an oily residue. This is purified by column chromatography on silica gel using a mixture of diethyl ether and ethyl acetate as eluent. Evaporation of the solvent under reduced pressure yields 5-(4-ethoxycarbonylbuta-1,3-dienyl)-imidazo[1,5-a]pyridine melting at 101°-103°.

Workup

  1. temperatureThe reaction mixture is maintained at 5°
  2. temperatureby cooling in an ice-water bath
  3. additionis added to the reaction mixture which
  4. extractionextracted with 2×100 ml of ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto yield an oily residue
  9. customThis is purified by column chromatography on silica gel using
  10. additiona mixture of diethyl ether and ethyl acetate as eluent
  11. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5f2b746fbf3e4fae99b856553793bc16
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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