反应详情

温度

-70 °C

To a cold (−70° C.) solution of 2-methyl-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid, tert-butyl ester (253) (3.36 g, 10.0 mmol) in THF is added 1.6M n-butyl lithium in hexane (6.9 mL, 11.0 mmol), and the mixture is stirred for 1 h at −70° C. To the reaction mixture is added 4-fluorobenzaldehyde (1.18 mL, 11.0 mmol), and the mixture is stirred for 1 h at −70° C. and 1 h at RT. To the reaction mixture is added ammonium chloride solution, EtOAc, and the organic layer is separated, and washed with brine, dried (MgSO4), and filtered. The filtrate is rotary evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane:EtOAc (9:1) gives 2.11 g of the product 256. 1H NMR (CDCl3) δ 7.60-7.45 (m, 2 H), 7.15-6.90 (m, 10 H), 6.85-6.60 (m, 2 H), 5.70-5.20 (m, 4 H), 3.60-3.10 (m, 2 H), 1.18 (s, 9 H); MS: m/z 461 (M++1).

1. stirringthe mixture is stirred for 1 h at −70° C. and 1 h at RT
2. customthe organic layer is separated
3. washwashed with brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customthe residue purified by chromatography on silica gel
7. washelution with dichloromethane:EtOAc (9:1)