Butyl bromide → 1-Methoxymethyl-alpha-phenyl-alpha-(m-trifluoromethyl-phenyl)imidazole-2-methanol

HRID 261945

反応式

HRID 261945 の反応式
C([Li])CCC.[Li].C(Br)CCC.[CH3:12][O:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.CN(C)CCN(C)C.[F:28][C:29]([F:45])([F:44])[C:30]1[CH:31]=[C:32]([CH:41]=[CH:42][CH:43]=1)[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]>O.O1CCCC1.C(OCC)C>[CH3:12][O:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:32]1[CH:41]=[CH:42][CH:43]=[C:30]([C:29]([F:44])([F:45])[F:28])[CH:31]=1)[OH:34]

参加物

10

反応物 6

HCID 8002Butyl bromideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 697663-(Trifluoromethyl)benzophenoneHCID 883591-(methoxymethyl)-1H-imidazoleHCID 3028194LithiumHCID 178418339Butyllithium

生成物 1

HCID 124338951-Methoxymethyl-alpha-phenyl-alpha-(m-trifluoromethyl-phenyl)imidazole-2-methanol

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under a nitrogen atmosphere and at a temperature between -60° and -65° C. a butyllithium solution, prepared from 2.04 g. (0.29 g. at) of lithium and 15.8 g. (0.116 mol) of butyl bromide in 130 ml. of anhydrous diethyl ether, was added drop-wise to a solution of 9.8 g. (0.088 mol) of 1-(methoxymethyl)imidazole and 10.2 g. (0.088 mol) of N,N,N',N'-tetramethylethylenediamine in 250 ml. of anhydrous tetrahydrofuran. After 2 hours stirring, a solution of 22 g. (0.088 mol) of 3-(trifluoromethyl)benzophenone in 150 ml. of anhydrous tetrahydrofuran were added dropwise to the reaction mixture at a temperature between -60° and -65° C. The reaction mixture was stirred for one hour at -65° C. and it was then kept standing overnight at room temperature. Then 20 ml. of water were added to the reaction mixture and the solvents were distilled off. The residue was dissolved in dilute hydrochloric acid and the solution was washed with diethyl ether and made alkaline with potassium carbonate. The solid substance formed was filtered off and dissolved in chloroform. The solution was dried over sodium sulphate, the solvent was distilled off and the residue was crystallised from isopropyl alcohol. 1-(Methoxymethyl)-α-phenyl-α-(m-trifluoromethyl-phenyl)imidazole-2-methanol was obtained. Melting point 152.5°-153.5° C.

後処理

  1. stirringThe reaction mixture was stirred for one hour at -65° C.
  2. waitit was then kept standing overnight at room temperature
  3. distillationthe solvents were distilled off
  4. dissolutionThe residue was dissolved in dilute hydrochloric acid
  5. washthe solution was washed with diethyl ether
  6. customThe solid substance formed
  7. filtrationwas filtered off
  8. dissolutiondissolved in chloroform
  9. dry with materialThe solution was dried over sodium sulphate
  10. distillationthe solvent was distilled off
  11. customthe residue was crystallised from isopropyl alcohol

出典と根拠

ORDレコード
ord-1c5495d39d404e1d975daa9c88374763
出典データセット
uspto-grants-1979_05
特許番号
US04152441

関連ノート

読み込み中…