Diisobutylaluminumhydride → methyl 2-bromo-3-(2-butyn-1-yl)-5-formyl-3H-imidazole-4-carboxylate

HRID 1663317ノート

反応式

HRID 1663317 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[Br:11][CH:12]1[N:16]([CH2:17][C:18]#[C:19][CH3:20])[C:15]([C:21]([O:23][CH3:24])=[O:22])=[C:14]([C:25](OC)=[O:26])[NH:13]1>O1CCCC1>[Br:11][C:12]1[N:16]([CH2:17][C:18]#[C:19][CH3:20])[C:15]([C:21]([O:23][CH3:24])=[O:22])=[C:14]([CH:25]=[O:26])[N:13]=1

参加物

4

反応物 2

HCID 21225700Diisobutylaluminumhydride2 回HCID 67436167dimethyl 2-bromo-3-(2-butyn-1-yl)-1H-imidazole-4,5-dicarboxylate

生成物 1

HCID 21947682methyl 2-bromo-3-(2-butyn-1-yl)-5-formyl-3H-imidazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-65 °C

実験手順

45 ml diisobutylaluminum hydride solution (1M in toluene) are added dropwise to 12.45 g dimethyl 2-bromo-3-(2-butyn-1-yl)-1H-imidazole-4,5-dicarboxylate in 150 ml of tetrahydrofuran under an argon atmosphere at −65° C. The reaction mixture is stirred for two hours at −65° C., then another 9 ml diisobutylaluminum hydride solution are added. After another hour the reaction mixture is quenched at −65° C. with a mixture of 1 M hydrochloric acid and tetrahydrofuran (1:1) and stirred for ten minutes. Then the cooling bath is removed, the reaction mixture is diluted with water and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulphate and evaporated down. The crude product is purified by chromatography over a silica gel column with cyclohexane/ethyl acetate (2:1 to 1:1).

後処理

  1. customAfter another hour the reaction mixture is quenched at −65° C. with a mixture of 1 M hydrochloric acid and tetrahydrofuran (1:1)
  2. stirringstirred for ten minutes
  3. customThen the cooling bath is removed
  4. additionthe reaction mixture is diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic phases are dried over magnesium sulphate
  7. customevaporated down
  8. customThe crude product is purified by chromatography over a silica gel column with cyclohexane/ethyl acetate (2:1 to 1:1)

出典と根拠

ORDレコード
ord-37d8f047297e4e94ac62c04efc8561b7
出典データセット
uspto-grants-2011_10
特許番号
US08034941B2

反応ノート

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