Potassium Acetate → 1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carbaldehyde

HRID 1828820ノート

反応式

HRID 1828820 の反応式
Br[C:2]1[N:3]=[C:4]([CH3:23])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=2[Cl:22])[C:6]=1[CH:7]=[O:8].C([O-])(=O)C.[K+]>CO.O1CCOCC1.[C].[Pd]>[Cl:22][C:11]1[CH:12]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:14]=[CH:15][C:10]=1[CH2:9][N:5]1[C:6]([CH:7]=[O:8])=[CH:2][N:3]=[C:4]1[CH3:23]

参加物

6

反応物 2

HCID 517044Potassium AcetateHCID 22058585HCID 22058585、化合物

生成物 1

HCID 220586591-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carbaldehyde収率 96.6%

試薬・触媒・溶媒 3

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

4-Bromo-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carbaldehyde (4.00 g) was dissolved in a mixed solvent of methanol (20 ml) and 1,4-dioxane (20 ml), and palladium carbon (400 mg) and potassium acetate (1.08 g) were added. The reaction mixture was stirred under a hydrogen atmosphere for 3 hr. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. Water was added to the residue and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was applied to silica gel column chromatography and eluted with hexane/ethyl acetate=1/2. The objective fraction was concentrated under reduced pressure to give 1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carbaldehyde (3.10 g) as a pale-yellow oil.

後処理

  1. additionwere added
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluted with hexane/ethyl acetate=1/2
  10. concentrationThe objective fraction was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-b768588785534e989070cc119bbf6e5a
出典データセット
uspto-grants-2006_06
特許番号
US07060721B1

反応ノート

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