反応 #595393

反応方程式

2-Butanone

4-bromophenylhydrazine hydrochloride

→

indole

収率 67.0%

5-Bromo-2,3-dimethyl-1H-indole

収率 67.0%

溶媒

EtOH

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux for 22 h
3. 3
   濃縮concentrated in vacuo
4. 4
   その他partitioned between EtOAc and 1N HCl
5. 5
   洗浄The organic layer was washed with H2O and saturated aqueous NaHCO3
6. 6
   乾燥dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他The crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane)

実験手順

Following a published procedure (Gundersen, E. G. U.S. Patent App. Publ. US 2005/070592) 2-Butanone (0.11 mL, 1.278 mmol) was added to a solution of 4-bromophenylhydrazine hydrochloride (0.300 g, 1.342 mmol in EtOH (3.8 mL). The mixture was heated to reflux for 22 h, concentrated in vacuo, and partitioned between EtOAc and 1N HCl. The organic layer was washed with H2O and saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane) to afford the desired indole as a pink powder (200 mg, 67%).

出典