Реакция #85692

Уравнение реакции

1-(4-chlorophenyl)-4-(1,3-dioxolan-2-yl)-2-methyl-1H-imidazole

camphorsulfonic acid

→

1-(4-chlorophenyl)-2-methyl-1H-imidazole-4-carbaldehyde

Выход 69.0%

Растворители

THF

water

Условия реакции

Обработка

1. 1
   Другоеquenched with saturated aqueous sodium bicarbonate (100 mL)
2. 2
   ЭкстракцияThe mixture was extracted with ethyl acetate (100 mL)
3. 3
   Промывкаthe organic layer was washed with saturated aqueous sodium chloride (50 mL)
4. 4
   Сушкаdried (Na2SO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated in vacuo

Методика

A solution of 1-(4-chlorophenyl)-4-(1,3-dioxolan-2-yl)-2-methyl-1H-imidazole (1.05 g, 3.97 mmol) and camphorsulfonic acid (92 mg, 0.40 mmol, 0.1 equiv) in THF (26.5 mL) and water (13.3 mL) was heated at 60° C. for 1 hour. The reaction was then cooled to room temperature and quenched with saturated aqueous sodium bicarbonate (100 mL). The mixture was extracted with ethyl acetate (100 mL) and the organic layer was washed with saturated aqueous sodium chloride (50 mL), dried (Na2SO4), filtered, and concentrated in vacuo. Silica gel column chromatography (EtOAc with 7% methanol) provided 1-(4-chlorophenyl)-2-methyl-1H-imidazole-4-carbaldehyde (0.600 g, tan solid) in 69% yield. 1H NMR (400 MHz, CDCl3) δ 9.89 (s, 1H), 7.67 (s, 1H), 7.53 (d, J=8.7 Hz, 2H), 7.27 (d, J=8.7 Hz, 2H), 2.40 (s, 3H). MS m/z 221.0 (M+H)+; Rt-0.47 min.

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