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

HRID 6486
노트
인쇄 미리보기

반응식

HRID 6486 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 물질실험 절차후처리출처 및 근거반응 노트

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 6344
Dichloromethane
용매
3회
HCID 21584188Chloroform methanol용매

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 70 ml of methylene chloride at -78° C. for 45 minutes, 1-acetyl-2-n-butyl 5-acetoxymethyl imidazole in 50 ml of methylene chloride 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 on silica gel in methanol/chloroform gave 5-acetoxymethyl-1-[2-(1-adamantyl)-ethyl]-2-n-butyl-imidazole. This acetoxy compound (5.4 g) was stirred at room temperature with potassium hydroxide (5.2 g) in ethanol (200 ml) for one hour, the mixture was concentrated, poured into water, stirred, and filtered to give 1-[2-(1-adamantyl)ethyl]-2-n-butyl-5-hydroxymethyl- 1H-imidazole.

후처리

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

출처 및 근거

ORD 기록
ord-4abdcb5f4ce64f6f9dc993a5b72d5eb7
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05248689

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