Trifluoromethanesulfonic anhydride → 5-Acetoxymethyl-1-[2-(1-adamantyl)ethyl]2-n-butylimidazole

HRID 2081856

반응식

HRID 2081856 반응식
[C:1]12(CCO)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(C(C)C)CC)(C)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[C:38]([N:41]1[C:45]([CH2:46][O:47][C:48](=[O:50])[CH3:49])=[CH:44][N:43]=[C:42]1[CH2:51][CH2:52][CH2:53][CH3:54])(=O)[CH3:39]>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[C:48]([O:47][CH2:46][C:45]1[N:41]([CH2:38][CH2:39][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)[C:42]([CH2:51][CH2:52][CH2:53][CH3:54])=[N:43][CH:44]=1)(=[O:50])[CH3:49]

참가 물질

7

반응물 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 1108102-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanolHCID 197935471-Acetyl-2-n-butyl 5-acetoxymethyl imidazole

생성물 1

HCID 199367975-Acetoxymethyl-1-[2-(1-adamantyl)ethyl]2-n-butylimidazole

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 21584188Chloroform methanol용매

반응 조건

온도
-78 °C

실험 절차

A mixture of 2-(1-adamantyl)ethanol (10.7 g and diisopropylethylamine (11 ml) in methylene chloride (70 ml) was added to triflic anhydride (16.75 g) in methylene chloride (70 ml) at -78° C. under argon. After stirring the mixture at -78° C. for 45 minutes, 1-acetyl-2-n-butyl-5 -(acetoxymethyl)imidazole in methylene chloride (50 ml) was added and the mixture was allowed to stand at room temperature for 4 days, then concentrated and heated on a steam bath with 10% sodium hydroxide (250 ml), diluted with 300 ml of water, extracted with methylene chloride, dried, filtered and concentrated to give an oil. Chromatography (silica gel) in methanol-chloroform gives 5-acetoxymethyl-1-[2-(1-adamantyl)ethyl]-2-n-butylimidazole.

후처리

  1. waitto stand at room temperature for 4 days
  2. concentrationconcentrated
  3. temperatureheated on a steam bath with 10% sodium hydroxide (250 ml)
  4. additiondiluted with 300 ml of water
  5. extractionextracted with methylene chloride
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil

출처 및 근거

ORD 기록
ord-be502e9612ec40cd99aa349622be2ab8
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05185351

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