تفاعل #85599

معادلة التفاعل

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

المردود 73.8%

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

المردود 73.8%

المذيبات

Water

—

hexanes

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas warmed to 25° C
2. 2
   غسيلThe organic phase was washed with brine
3. 3
   تجفيفdried with sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue was purified by SiO2 column chromatography (PE)

الإجراء التجريبي

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.

المصدر