Реакция #47074

Уравнение реакции

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

Выход 47.4%

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

Выход 47.4%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   workup.WAITat RT for 30 min
2. 2
   Экстракцияthe mixture extracted with EtOAc
3. 3
   ДругоеThe organic layer is separated
4. 4
   Сушкаdried (MgSO4)
5. 5
   Фильтрацияfiltered
6. 6
   Другоеthe residue is recrystallized from Et2O

Методика

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).

Источник