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

HRID 280207노트

반응식

HRID 280207 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5ff47a749feb4f6cabb6e410800777fd
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588732

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