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

HRID 261945

반응식

HRID 261945 반응식
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]

참가 물질

10

반응물 6

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c5495d39d404e1d975daa9c88374763
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152441

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