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

HRID 1828820노트

반응식

HRID 1828820 반응식
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]

참가 물질

6

반응물 2

HCID 517044Potassium AcetateHCID 22058585HCID 22058585, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b768588785534e989070cc119bbf6e5a
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060721B1

반응 노트

불러오는 중…