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

HRID 2254296

Reaktionsgleichung

[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.C(Cl)(Cl)Cl.CO>[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]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A mixture of 2-(1-adamantyl)ethanol and diisopropylethylamine in methylene chloride is added to triflic anhydride in methylene chloride 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 is added and the mixture is allowed to stand at room temperature for 4 days, then concentrated and heated on a steam bath with 10% sodium hydroxide, diluted with 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.

Aufarbeitung

waitto stand at room temperature for 4 days
concentrationconcentrated
temperatureheated on a steam bath with 10% sodium hydroxide
additiondiluted with water
extractionextracted with methylene chloride
customdried
filtrationfiltered
concentrationconcentrated
customto give an oil

Quellen und Nachweise

ORD-Eintrag: ord-ce54db51a3b3462ca9c6a80828cdfc86
Quelldatensatz: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05234917

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