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1-(3-Chlorobenzyl)imidazole → 1-(2-Allyl-5-norbornen-2-yl)-2-(3-chlorophenyl)-2-(1-imidazolyl)-ethanol

HRID 359044
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인쇄 미리보기

반응식

HRID 359044 반응식
C([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[CH2:19]([C:22]1([CH:29]=[O:30])[CH2:27][CH:26]2[CH2:28][CH:23]1[CH:24]=[CH:25]2)[CH:20]=[CH2:21]>CCCCCC.C1COCC1>[CH2:19]([C:22]1([CH:29]([OH:30])[CH:10]([C:9]2[CH:16]=[CH:17][CH:18]=[C:7]([Cl:6])[CH:8]=2)[N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH2:27][CH:26]2[CH2:28][CH:23]1[CH:24]=[CH:25]2)[CH:20]=[CH2:21]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 122293861-(3-Chlorobenzyl)imidazoleHCID 200656362-Allyl-5-norbornen-2-aldehydeHCID 178418339Butyllithium

생성물 1

HCID 142303401-(2-Allyl-5-norbornen-2-yl)-2-(3-chlorophenyl)-2-(1-imidazolyl)-ethanol수율 38%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 8058
Hexane
용매

반응 조건

온도
-70 °C

실험 절차

13.8 ml (20 mmol) of a 1.45 molar solution of n-butyllithium in hexane were added dropwise to a solution of 3.85 g (20 mmol) of 1-(3-chlorobenzyl)-imidazole in 40 ml of absolute THF at -70° C. After stirring for 30 minutes at -70° C., a solution of 4.39 g of 74% purity (20 mmol) 2-allyl-5-norbornen-2-aldehyde in 30 ml of absolute THF was added dropwise at about -70° C. over about 12 minutes. The further procedure was subsequently carried out as described in Example 2. The residue (9.0 g) remaining from the organic component after removing the solvent by distillation was dissolved in diisopropyl ether/hexane 2:1, whereupon crystalline product precipitated. After isolation using 20 ml of acetonitrile, this was boiled briefly, filtered off under suction after cooling the mixture, and washed with acetonitrile. 2.70 g (≅38% yield) of pure 1-(2-allyl-5-norbornen-2-yl)-2-(3-chlorophenyl)-2-(1-imidazolyl)-ethanol were obtained in the form of a mixture, comprising 2 diastereomers, of melting point 134°-135° C.

후처리

  1. customafter removing the solvent
  2. distillationby distillation
  3. dissolutionwas dissolved in diisopropyl ether/hexane 2:1
  4. customwhereupon crystalline product precipitated
  5. filtrationfiltered off under suction
  6. temperatureafter cooling the mixture
  7. washwashed with acetonitrile

출처 및 근거

ORD 기록
ord-94cac9818ebc47fc8870d28fe5377af7
출처 데이터셋
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04999352

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