Reacción #77792

Ecuación de reacción

6-Fluoro-5-(5-hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester

NaOH

→

5-(6-Fluoro-1H-indol-5-yl)-pent-4-yn-1-ol

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro75% of the solvent were evaporated
2. 2
   workup.ADDITIONthe resulting mixture was poured into 5 ml of water
3. 3
   Extracciónextracted with EtOAc
4. 4
   SecadoDrying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2

Procedimiento

A solution of 950 mg (0.3 mmol) 6-Fluoro-5-(5-hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester in 20 ml EtOH was treated with 2 ml of saturated aqeous NaOH and stirred during 2 hours at 60° C. 75% of the solvent were evaporated, the resulting mixture was poured into 5 ml of water, acidified with 2M aqueous HCl, and extracted with EtOAc. Drying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2 gave 550 mg (84%) of 5-(6-Fluoro-1H-indol-5-yl)-pent-4-yn-1-ol as a viscous light yellow oil, MS: 218 (M).

Fuente