Ammonium Chloride → [2-benzyloxymethyl-5-isopropyl-3-methyl-3H-imidazol-4-yl]-(3,5-dichlorophenyl)-methanol

HRID 1416036노트

반응식

HRID 1416036 반응식
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12](I)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([Li])CCC.[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=1)[CH:28]=[O:29].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:1]([O:8][CH2:9][C:10]1[N:11]([CH3:19])[C:12]([CH:28]([C:27]2[CH:26]=[C:25]([Cl:24])[CH:32]=[C:31]([Cl:33])[CH:30]=2)[OH:29])=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 357463,5-DichlorobenzaldehydeHCID 178418339ButyllithiumHCID 1784401402-((benzyloxy)methyl)-4-iodo-5-isopropyl-1H-imidazole

생성물 1

HCID 22130494[2-benzyloxymethyl-5-isopropyl-3-methyl-3H-imidazol-4-yl]-(3,5-dichlorophenyl)-methanol수율 33.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

In 30 ml of dry tetrahydrofuran was dissolved 3.31 g (8.94 mmol)of 2-benzyloxymethyl-5-iodo-4-isopropyl-1-methylimidazole (4c), followed by addition of 5.78 ml (9.83 mmol)of n-butyllithium (1.70 M hexane solution)at -70° C. over 30 minutes. Then, after 5 minutes, a solution of 1.56 g (8.91 g)of 3,5-dichlorobenzaldehyde dissolved in 10 ml of dry tetrahydrofuran was added at -70° C. over 30 minutes. After 1 hour, the mixture was left to cool to room temperature, and an aqueous solution of ammonium chloride was added thereto, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate/methylene chloride 10:1)to give 1.25 g of [2-benzyloxymethyl-5-isopropyl-3-methyl-3H-imidazol-4-yl]-(3,5-dichlorophenyl)-methanol (56) (yield 33.3%).

후처리

  1. additionwas added at -70° C. over 30 minutes
  2. waitAfter 1 hour
  3. waitthe mixture was left
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe crude product was purified by silica gel chromatography (ethyl acetate/methylene chloride 10:1)to

출처 및 근거

ORD 기록
ord-482d2192217b4367b5a706f4c3f3231d
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05910506

반응 노트

불러오는 중…