Sodium Methoxide → 5-Methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde

HRID 545364노트

반응식

HRID 545364 반응식
Br[C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:4]([CH3:18])[C:3]=1[CH:19]=[O:20].[CH3:21][O-:22].[Na+]>CO>[CH3:21][O:22][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:4]([CH3:18])[C:3]=1[CH:19]=[O:20]

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 866260315-Bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde

생성물 1

HCID 866260325-Methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 1.00 g (2.9 mmol) of 5-bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde in 25 ml of MeOH was treated with 3.20 ml (17.3 mmol) sodium methoxide-solution (5.4 molar in MeOH) and then stirred at reflux for 48 hours. After cooling down to RT, the solvent was evaporated, cold water and EtOAc were added and the mixture then 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 (n-heptane/EtOAc 4:1 to 1:1) to give 0.926 g (quant.) of the title compound as light yellow solid. MS: 301.1 (MH+).

후처리

  1. temperatureat reflux for 48 hours
  2. customthe solvent was evaporated
  3. additioncold water and EtOAc were added
  4. extractionthe mixture then extracted twice with EtOAc
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (n-heptane/EtOAc 4:1 to 1:1)

출처 및 근거

ORD 기록
ord-0693f24a0d9041de860c5157de914cc1
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935707B2

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