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

HRID 545328

반응식

HRID 545328 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]−).

후처리

  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)

출처 및 근거

ORD 기록
ord-0b43dc0348244c5da7ce19c5aaf4b002
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935707B2

연결된 노트

불러오는 중…