Water → 5-(5-Carboxypent-1-enyl)-imidazo[1,5-a]pyridine

HRID 280227Notes

Reaction equation

HRID 280227 reaction equation
[CH:1]([C:3]1[N:8]2[CH:9]=[N:10][CH:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1)=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O-:25])=[O:24])C=CC=CC=1.[Na+].O.S(=O)(=O)(O)O>CS(C)=O>[C:23]([CH2:22][CH2:21][CH2:20][CH:19]=[CH:1][C:3]1[N:8]2[CH:9]=[N:10][CH:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1)([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 13206163Imidazo[1,5-a]pyridine-5-carbaldehydeHCID 178525466HCID 178525466, compound

Product 1

HCID 542369435-(5-Carboxypent-1-enyl)-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 5-formylimidazo[1,5-a]pyridine (1.46 g) in 15 ml of dry dimethylsulfoxide is added to a solution of sodium 5-(triphenylphosphoranyl)valerate (4.4 g) in 50 ml of dry dimethylsulfoxide at room temperature (Helv. Chem. Acta 63 1430 (1980)). The reaction is stirred for 3 hours, hydrolyzed with water and neutralized with dilute sulfuric acid. Extraction with ethyl acetate and chromatography or silica gel yields 5-(5-carboxypent-1-enyl)-imidazo[1,5-a]pyridine.

Workup

  1. extractionExtraction with ethyl acetate and chromatography or silica gel

Sources & evidence

ORD record
ord-e7ea5584c61049ab8c9169c02bec2abd
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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