Methanol → 5-(5-Formylpentyl)imidazo[1,5-a]pyridine

HRID 280210Notes

Reaction equation

HRID 280210 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[N:15]2[CH:16]=[N:17][CH:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.CO.O>C(Cl)Cl.CCCCCC>[CH:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[N:15]2[CH:16]=[N:17][CH:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1)=[O:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 233218845-(5-Methoxycarbonylpentyl)imidazo[1,5-a]pyridine

Product 1

HCID 233218905-(5-Formylpentyl)imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a cooled (-60°) solution of 4.9 g of 5-(5-methoxycarbonylpentyl)-imidazo[1,5-a]pyridine [obtained by esterification of 5-(5-carboxypentyl)-imidazo[1,5-a]pyridine with diazomethane in methylene chloride] in 140 ml of methylene chloride is added 40 ml of a 1.75M solution of diisobutyl aluminum hydride in hexane in a dropwise manner over a 20 minute period. On completion of the addition, the reaction is allowed to stir at -60° for a further 20 minutes. Then, 10 ml of methanol, followed by 100 ml of water, are added to quench the reaction. The reaction mixture is stirred at room temperature for 15 minutes, the methylene chloride layer is separated and the solvent evaporated under reduced pressure to yield 5-(5-formylpentyl)imidazo[1,5-a]pyridine as an oil; NMR (CDCl3) 9.7 (m, 1H); IR (CH2Cl2) 1710 cm-1.

Workup

  1. additionOn completion of the addition
  2. additionare added
  3. customto quench
  4. customthe reaction
  5. stirringThe reaction mixture is stirred at room temperature for 15 minutes
  6. customthe methylene chloride layer is separated
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-910f4cd6f04241c290b64e0155a7f2b6
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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