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

HRID 350664노트

반응식

HRID 350664 반응식
[H-].C([Al+]CC(C)C)C(C)C.[Br:11][C:12]1[N:13]([CH2:25][C:26]#[C:27][CH3:28])[C:14]([C:21]([O:23][CH3:24])=[O:22])=[C:15]([C:17](OC)=[O:18])[N:16]=1.Cl.O>O1CCCC1>[Br:11][C:12]1[N:13]([CH2:25][C:26]#[C:27][CH3:28])[C:14]([C:21]([O:23][CH3:24])=[O:22])=[C:15]([CH:17]=[O:18])[N:16]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 21947677dimethyl 2-bromo-1-(but-2-ynyl)-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 8028Tetrahydrofuran용매3회

반응 조건

온도
-70 °C

실험 절차

43 ml of a 1 M solution of diisobutyl-aluminium hydride in tetrahydrofuran are added dropwise to a solution of 13.5 g of dimethyl 2-bromo-1-(2-butyn-1-yl)-1H-imidazole-4,5-dicarboxylate in 220 ml of tetrahydrofuran under an argon atmosphere at −70° C. within 20 minutes. The mixture is stirred for a further four hours at −70° C., then 20 ml of a mixture of 1 M hydrochloric acid and tetrahydrofuran are added dropwise. After heating to ambient temperature approx. 200 ml of water are added and the mixture is extracted three times with 70 ml of ethyl acetate. The combined extracts are dried and evaporated down. The crude product thus obtained is purified by column chromatography through silica gel with petroleum ether/ethyl acetate (80:20 to 50:50) as eluant.

후처리

  1. temperatureAfter heating to ambient temperature approx
  2. extractionthe mixture is extracted three times with 70 ml of ethyl acetate
  3. customThe combined extracts are dried
  4. customevaporated down

출처 및 근거

ORD 기록
ord-48e889b1979940c088683a988b83c67f
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183280B2

반응 노트

불러오는 중…