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

HRID 280207ノート

反応式

HRID 280207 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5ff47a749feb4f6cabb6e410800777fd
出典データセット
uspto-grants-1986_05
特許番号
US04588732

反応ノート

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