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

HRID 350664ノート

反応式

HRID 350664 の反応式
[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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 21947677dimethyl 2-bromo-1-(but-2-ynyl)-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3 回

反応条件

温度
-70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-48e889b1979940c088683a988b83c67f
出典データセット
uspto-grants-2007_02
特許番号
US07183280B2

反応ノート

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