Lithium diisopropylamide → 5-(9-Ethoxycarbonylnona-6,8-dienyl)imidazo[1,5-a]pyridine

HRID 280207Notes

Reaction equation

HRID 280207 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][CH2:10][O:11][C:12](/[CH:14]=[CH:15]/[CH2:16]P(OCC)(OCC)=O)=[O:13].[CH:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[N:37]2[CH:38]=[N:39][CH:40]=[C:36]2[CH:35]=[CH:34][CH:33]=1)=O>O1CCCC1>[CH2:10]([O:11][C:12]([CH:14]=[CH:15][CH:16]=[CH:25][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[N:37]2[CH:38]=[N:39][CH:40]=[C:36]2[CH:35]=[CH:34][CH:33]=1)=[O:13])[CH3:9]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 233218905-(5-Formylpentyl)imidazo[1,5-a]pyridine

Product 1

HCID 540559275-(9-Ethoxycarbonylnona-6,8-dienyl)imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium diisopropylamide (prepared from 3.8 ml of n-butyllithium in hexane and 0.84 ml of diisopropylamine) in 10 ml tetrahydrofuran at -70° C., is added 1.35 g of triethyl 4-phosphonocrotonate in a dropwise manner over a 15 minute period. On completion of the addition, 6.0 g of 5-(5-formylpentyl)imidazo[1,5-a]pyridine is added in a dropwise manner. The reaction mixture is allowed to stir at room temperature for 15 minutes. The reaction mixture is quenched with methanol and the solvent evaporated under reduced pressure to yield 5-(9-ethoxycarbonyl-nona-6,8-dienyl)-imidazo[1,5-a]pyridine as an oil.

Workup

  1. additionis added in a dropwise manner
  2. customThe reaction mixture is quenched with methanol
  3. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-5ff47a749feb4f6cabb6e410800777fd
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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