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

HRID 545364ノート

反応式

HRID 545364 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-0693f24a0d9041de860c5157de914cc1
出典データセット
uspto-grants-2011_05
特許番号
US07935707B2

反応ノート

読み込み中…