5-[5-Ethoxycarbonyl-5-(phenylsulfinyl)pentyl]-imidazo[1,5-a]pyridine → 5-(5-Ethoxycarbonylpent-4-enyl)-imidazo[1,5-a]pyridine

HRID 326125Notes

Reaction equation

HRID 326125 reaction equation
[CH2:1]([O:3][C:4]([CH:6](S(C1C=CC=CC=1)=O)[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)=[O:5])[CH3:2]>C1(C)C(C)=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][C:11]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 204466825-[5-Ethoxycarbonyl-5-(phenylsulfinyl)pentyl]-imidazo[1,5-a]pyridine

Product 1

HCID 544704715-(5-Ethoxycarbonylpent-4-enyl)-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 3 g of 5-[5-ethoxycarbonyl-5-(phenylsulfinyl)pentyl]-imidazo[1,5-a]pyridine in 50 ml xylene is heated at reflux temperature for 30 minutes under an atmosphere of nitrogen. The xylene is then removed by distillation under reduced pressure, the residue is dissolved in 15 ml of diethyl ether and purified by column chromatography on silica gel. The product is eluted using a 2:1 mixture of diethyl ether and ethyl acetate as eluent. Evaporation of the solvent yields 5-(5-ethoxycarbonylpent-4-enyl)-imidazo[1,5-a]pyridine as an oil; NMR (CDC13) 1.29 (t,3H), 4.25 (q,2H), 5.88 (d, 1H).

Workup

  1. temperatureat reflux temperature for 30 minutes under an atmosphere of nitrogen
  2. customThe xylene is then removed by distillation under reduced pressure
  3. dissolutionthe residue is dissolved in 15 ml of diethyl ether
  4. custompurified by column chromatography on silica gel
  5. washThe product is eluted
  6. additiona 2:1 mixture of diethyl ether and ethyl acetate as eluent
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7a5b23b0b5e44347a11ecacee57d9738
Source dataset
uspto-grants-1984_04
Patent number
US04444775

Reaction notes

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