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

HRID 1663317노트

반응식

HRID 1663317 반응식
[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

참가 물질

4

반응물 2

HCID 21225700Diisobutylaluminumhydride2회HCID 67436167dimethyl 2-bromo-3-(2-butyn-1-yl)-1H-imidazole-4,5-dicarboxylate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-65 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-37d8f047297e4e94ac62c04efc8561b7
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034941B2

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