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

HRID 1416036ノート

反応式

HRID 1416036 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-482d2192217b4367b5a706f4c3f3231d
出典データセット
uspto-grants-1999_06
特許番号
US05910506

反応ノート

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