Carbon Dioxide → alpha-(o-Tert.-butylphenyl)-alpha-phenyl-1-vinylimidazole-2-methanol

HRID 261952

반응식

HRID 261952 반응식
CN(C)CCN(C)C.[CH:9]([N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)=[CH2:10].C([Li])CCC.[C:21]([C:25]1[CH:38]=[CH:37][CH:36]=[CH:35][C:26]=1[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28])([CH3:24])([CH3:23])[CH3:22].C(=O)=O>CCCCCC.O.O1CCCC1>[C:21]([C:25]1[CH:38]=[CH:37][CH:36]=[CH:35][C:26]=1[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:12]1[N:11]([CH:9]=[CH2:10])[CH:15]=[CH:14][N:13]=1)[OH:28])([CH3:24])([CH3:22])[CH3:23]

참가 물질

9

반응물 5

HCID 280Carbon DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 661711-VinylimidazoleHCID 54101900(2-tert-Butylphenyl)(phenyl)methanoneHCID 178418339Butyllithium

생성물 1

HCID 12433926alpha-(o-Tert.-butylphenyl)-alpha-phenyl-1-vinylimidazole-2-methanol

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-60 °C

실험 절차

To a solution of 28.8 g. (0.25 mol) of N,N,N',N'-tetramethylethylenediamine and 17.6 g. (0.19 mol) of 1-vinylimidazole in 300 ml. of anhydrous tetrahydrofuran, 14 ml. (0.25 mol) of 20% butyllithium in n-hexane were added drop-wise with stirring at -60° C., and under a nitrogen atmosphere over the course of one hour. Stirring was continued for 2 hours under the same conditions, after which a solution of 48 g. (0.20 mol) of 2-tert.-butylbenzophenone in 300 ml. of anhydrous tetrahydrofuran was added drop-wise. The reaction mixture was stirred for 3.5 hours, after which the cooling means was removed and stirring was continued overnight under the nitrogen atmosphere. The lithium complex obtained was then decomposed with 15 ml. of water and a large excess of solid carbon dioxide. The precipitate was filtered off, the filtrate was dried over sodium sulphate and the solvent was distilled off. The solid residue was twice crystallised from ethyl acetate to which a small amount of ethanol had been added. α-(o-tert.-Butylphenyl)-α-phenyl-1-vinylimidazole-2-methanol was obtained. Melting point 152°-153° C.

후처리

  1. customover the course of one hour
  2. stirringStirring
  3. stirringThe reaction mixture was stirred for 3.5 hours
  4. customafter which the cooling means was removed
  5. stirringstirring
  6. waitwas continued overnight under the nitrogen atmosphere
  7. customThe lithium complex obtained
  8. filtrationThe precipitate was filtered off
  9. dry with materialthe filtrate was dried over sodium sulphate
  10. distillationthe solvent was distilled off
  11. customThe solid residue was twice crystallised from ethyl acetate to which a small amount of ethanol
  12. additionhad been added

출처 및 근거

ORD 기록
ord-6d2feb51346041a8ac3d69a3a8266c78
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152441

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