Trifluoroacetic acid → 2-(2-Chloro-6-ethyl-benzyl)-1h-imidazole

Temperature

100 °C

This compound was prepared using methodology described in J. Chem. Soc., Perkin Trans. 1, 2002, 1061-1066. To a stirred solution of 2.10 g (8.87 mmol) rac-(2-chloro-6-ethyl-phenyl)-(1H-imidazol-2-yl)-methanol in 10 ml 1,2-dichloroethane in a pressure tube were added dropwise 14.1 ml (88.7 mmol) triethylsilane and 8.04 ml (106 mmol) trifluoroacetic acid. The tube was sealed and the reaction mixture was stirred at 100° C. for 16 hours, before being cooled to room temperature and diluted with dichloromethane. The mixture was washed sequentially with 2 N aqueous sodium hydroxide solution and water and then 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) followed by trituration in ether to afford 0.66 g (34%) of the title compound as a white crystalline solid. MS (ISP): 223.1 ([M+H]+), 221.2 ([M+H]+).

1. customThis compound was prepared
2. customThe tube was sealed
3. temperaturebefore being cooled to room temperature
4. washThe mixture was washed sequentially with 2 N aqueous sodium hydroxide solution and water
5. dry with materialthe organic phase was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

ORD record

ord-c855fcb5c2334339b38657ef372445c0

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875645B2