Reaktion #341736

Reaktionsgleichung

trichloroisocyanuric acid

2-(2-cyclopropyl-6-methyl-benzyl)-4,5-dihydro-1H-imidazole

1,8-diazabicyclo[5.4.0]undec-7-ene

→

title compound

Ausbeute 16.0%

2-(2-Cyclopropyl-6-methyl-benzyl)-1H-imidazole

Ausbeute 16.0%

Lösungsmittel

ethyl acetate

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis compound was prepared
2. 2
   Waschenwashed sequentially with water and with saturated brine
3. 3
   SonstigeThe phases were separated
4. 4
   Trocknenthe organic phase was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

Vorschrift

This compound was prepared using methodology described in Synlett 2004, 2803-2805. To a solution of 400 mg (1.87 mmol)) 2-(2-cyclopropyl-6-methyl-benzyl)-4,5-dihydro-1H-imidazole in 5 ml acetonitrile at −17° C. were added sequentially 0.50 ml (3.36 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and a solution of 217 mg (0.93 mmol) trichloroisocyanuric acid (TCCA) in 2 ml acetonitrile. The reaction mixture was then stirred for 2 hours at room temperature, before being diluted with ethyl acetate and washed sequentially with water and with saturated brine. The phases were separated and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient) to afford 62 mg (16%) of the title compound as a white crystalline solid. MS (ISP): 213.4 ([M+H]+, 100%).

Quelle