反応 #85599

反応方程式

2,2,6,6-Tetramethylpiperidine

N,N′,N″,N″-pentamethyldiethylene triamine

compound 1

4-methylcatechol

n-BuLi

THF

1,1,2-trichloro-1,2,2-trifluoroethane

→

title compound

収率 73.8%

4-chloro-5-fluoro-1H-indole-3-carboxylic acid

収率 73.8%

溶媒

Water

—

hexanes

反応条件

後処理

1. 1
   温度was warmed to 25° C
2. 2
   洗浄The organic phase was washed with brine
3. 3
   乾燥dried with sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The residue was purified by SiO2 column chromatography (PE)

実験手順

2,2,6,6-Tetramethylpiperidine (1.06 g, 7.5 mmol), N,N′,N″,N″-pentamethyldiethylene triamine (3.46 g, 20 mmol) and compound 1 (1.45 g, 5.0 mmol) were added consecutively to a solution of n-BuLi (2.5 M in hexanes, 8 mL, 20 mmol) in THF (20 mL) and hexanes (6 mL) at −78° C. After stirring for 4 h at −78° C., the mixture was treated with 1,1,2-trichloro-1,2,2-trifluoroethane (1.18 g, 6.0 mmol) before it was warmed to 25° C. Water was added to the mixture. The organic phase was washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by SiO2 column chromatography (PE) to provide title compound (1.2 g, 73.8%) as a colorless liquid.

出典