Carbon Dioxide → 2-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazole-4-carboxylic acid

HRID 545328

反応式

HRID 545328 の反応式
[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:14]([CH3:20])[C:15](I)=[C:16]([I:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([Li])CCC.[C:26](=[O:28])=[O:27]>C1COCC1>[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:14]([CH3:20])[C:15]([C:26]([OH:28])=[O:27])=[C:16]([I:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 671329302-(3-Hexyl-phenyl)-4,5-diiodo-1-methyl-1H-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 671332392-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazole-4-carboxylic acid収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 7.27 g (14.7 mmol) of 2-(3-hexyl-phenyl)-4,5-diiodo-1-methyl-1H-imidazole in 150 ml of THF was cooled down to −75° C.; then, 11.95 ml (19.1 mmol) of an n-butyl lithium solution (1.6 molar in n-hexane) was added drop by drop below −70° C. 30 min later, the reaction mixture was treated with an excess of solid carbon dioxide and subsequently warmed up to RT. It was then poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 2.97 g (49%) of the title compound as light red oil. MS: 411.2 ([M-H]−).

後処理

  1. additionIt was then poured
  2. extractionextracted twice with EtOAc
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

出典と根拠

ORDレコード
ord-0b43dc0348244c5da7ce19c5aaf4b002
出典データセット
uspto-grants-2011_05
特許番号
US07935707B2

関連ノート

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