Reacción #47074

Ecuación de reacción

sodium bicarbonate

257

2-[2-(4-Fluorophenyl)-2-oxoethyl]-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid, tert-butyl ester

TFA

→

product 258

Rendimiento 47.4%

2-(cis-4,5-Diphenyl-4,5-dihydro-1H-imidazol-2-yl)-1-(4-fluorophenyl)ethan-1-one

Rendimiento 47.4%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat RT for 30 min
2. 2
   Extracciónthe mixture extracted with EtOAc
3. 3
   OtroThe organic layer is separated
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otrothe residue is recrystallized from Et2O

Procedimiento

To a cold (0° C.) solution of 257 (458 mg, 1.0 mmol) in dichloromethane (25 mL) is added TFA (1.5 mL). The reaction mixture is stirred for 20 min. at 0° C., and at RT for 30 min. The solution is poured into cold sat. sodium bicarbonate solution, and the mixture extracted with EtOAc. The organic layer is separated, dried (MgSO4), and filtered. The filtrate is rotary evaporated, and the residue is recrystallized from Et2O to give 170 mg of the product 258. 1H NMR (CDCl3) δ 10.60-8.80 (bs, 1 H), 8.00-7.80 (m, 2 H), 7.20-7.00 (m, 9 H), 7.00-6.85 (m, 4 H), 5.50 (bs, 1 H), 5.30 (s, 2 H); MS: m/z 359 (M++1).

Fuente