Reaktion #45865

Reaktionsgleichung

Imidazole

triphenyl phosphine

iodine

2-cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

sodium thiosulfate

→

compound

Ausbeute 80.3%

2-Cyclopropyl-7-(1-iodomethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Ausbeute 80.3%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring at the same temperature for 10 minutes
2. 2
   SonstigeThe aqueous layer was separated
3. 3
   Extraktionthis was extracted three times with ethyl acetate
4. 4
   Waschenwashed with saturated brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeThe insoluble matter was separated by filtration
7. 7
   Sonstigethe solvent was evaporated away
8. 8
   Sonstigethe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Vorschrift

Imidazole (321 mg, 4.71 mmol), triphenyl phosphine (1.235 g, 4.71 mmol) and then iodine (956 mg, 3.77 mmol) were added to a solution of 2-cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-297) (675 mg, 1.88 mmol) dissolved in benzene (20 ml). The solution was stirred under nitrogen atmosphere at room temperature for 20 hours, then aqueous saturated sodium thiosulfate solution was added, followed by stirring at the same temperature for 10 minutes. The aqueous layer was separated, this was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=19:1, v/v) to obtain the entitled compound (707 mg, 80%).

Quelle