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

HRID 280210ノート

反応式

HRID 280210 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-910f4cd6f04241c290b64e0155a7f2b6
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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