5-Methylimidazo(1,5-a)pyridine → 5-(5-Ethoxycarbonylpentyl)imidazo[1,5-a]pyridine

HRID 2417805ノート

反応式

HRID 2417805 の反応式
[CH3:1][C:2]1[N:7]2[CH:8]=[N:9][CH:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[Li]CC1N2C=NC=C2C=CC=1.Br[CH2:28][CH2:29][CH2:30][CH2:31][C:32](OCC)([O:36]CC)[O:33][CH2:34][CH3:35]>O1CCCC1.CCCCCC>[CH2:34]([O:33][C:32]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:1][C:2]1[N:7]2[CH:8]=[N:9][CH:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1)=[O:36])[CH3:35]

参加物

7

反応物 4

HCID 122109855-Methylimidazo(1,5-a)pyridineHCID 132061375-Bromo-1,1,1-triethoxypentaneHCID 178418339ButyllithiumHCID 178506849HCID 178506849、化合物

生成物 1

HCID 132061385-(5-Ethoxycarbonylpentyl)imidazo[1,5-a]pyridine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

To a solution of 50 g of 5-methylimidazo[1,5-a]pyridine [J. Org. Chem. 40, 1210 (1975)] in 625 ml of tetrahydrofuran precooled to -75° is added under nitrogen atmosphere 175 ml of 2.4N n-butyllithium in hexane while maintaining temperature below -53°. The solution of 5-(lithiomethyl)imidazo[1,5-a]pyridine, is cooled back to -75° and a solution of 121.8 g of 5-bromo-1,1,1-triethoxypentane in 125 ml of tetrahydrofuran is added rapidly at which time the temperature rises to -60°. The reaction mixture is allowed to warm to -4° over a 45 minute period and evaporated practically to dryness. The residue is partitioned between 500 ml of ethyl ether and 240 ml of 3N hydrochloric acid. The ether solution is further extracted twice with 60 ml of 3N hydrochloric acid; the combined aqueous extract is basified with 100 ml of concentrated ammonia hydroxide and reextracted twice with 200 ml of ethyl ether. The ether extract is dried over magnesium sulfate and evaporated to dryness to give an oil which is distilled under high vacuum to give 5-(5-ethoxycarbonylpentyl)-imidazo[1,5-a]pyridine boiling at 180°-5°/0.12 mm Hg.

後処理

  1. customprecooled to -75°
  2. temperaturewhile maintaining temperature below -53°
  3. customrises to -60°
  4. temperatureto warm to -4° over a 45 minute period
  5. customevaporated practically to dryness
  6. customThe residue is partitioned between 500 ml of ethyl ether and 240 ml of 3N hydrochloric acid
  7. extractionThe ether solution is further extracted twice with 60 ml of 3N hydrochloric acid
  8. extractionthe combined aqueous extract
  9. extractionThe ether extract
  10. dry with materialis dried over magnesium sulfate
  11. customevaporated to dryness
  12. customto give an oil which
  13. distillationis distilled under high vacuum

出典と根拠

ORDレコード
ord-db29cafbbf4a4ae39a5e1a147c35288b
出典データセット
uspto-grants-1984_09
特許番号
US04470986

反応ノート

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