Реакция #77794

Уравнение реакции

water

5-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-ol

N-Ethyldiisopropylamine

4-chlorophenyl chloroformate

→

6-Fluoro-5-(5-hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

Выход 74.3%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   Экстракцияextracted with EtOAc
2. 2
   Сушкаthe combined organic layers were dried with MgSO4
3. 3
   ДругоеEvaporation of the solvent, chromatography on silica gel with CH2Cl2/MeOH 49:1

Методика

A solution of 99 mg (0.45 mmol) 5-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-ol and 0.155 ml (0.90 mmol) N-Ethyldiisopropylamine in 2 ml CH2Cl2 was treated with 0.125 ml (0.90 mmol) 4-chlorophenyl chloroformate and stirred at room temperature during 1 hour. The mixture was poured into water, extracted with EtOAc and the combined organic layers were dried with MgSO4. Evaporation of the solvent, chromatography on silica gel with CH2Cl2/MeOH 49:1 gave 125 mg (74%) of 6-Fluoro-5-(5-hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as a viscous light yellow oil, MS: 374 (MH+, 1Cl).

Источник