反应 #2487459

反应方程式

tert-butyl[4-cyclopropyl-2-(2-oxo-2-phenylethyl)phenyl]carbamate

trifluoroacetic acid

→

title compound

收率 85.1%

5-Cyclopropyl-2-phenyl-1H-indole

收率 85.1%

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度cooling
2. 2
   浓缩The reaction mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONTo the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
4. 4
   其他to separate the organic layer
5. 5
   洗涤The organic layer was washed with saturated brine
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   浓缩concentrated under reduced pressure
8. 8
   其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

To a solution of tert-butyl[4-cyclopropyl-2-(2-oxo-2-phenylethyl)phenyl]carbamate (561 mg) in dichloromethane (8 mL) was added dropwise trifluoroacetic acid (1.6 mL) under ice-cooling. The mixture was heated to room temperature, and then stirred for 23 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution to separate the organic layer. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (317 mg). 1H-NMR (CDCl3) δ ppm: 0.65-0.75 (2H, m), 0.85-1.00 (2H, m), 1.95-2.10 (1H, m), 6.70-6.80 (1H, m), 6.90-7.00 (1H, m), 7.25-7.50 (5H, m), 7.60-7.70 (2H, m), 8.24 (1H, br s).

来源