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

HRID 280210노트

반응식

HRID 280210 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-910f4cd6f04241c290b64e0155a7f2b6
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588732

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