反応 #77792

反応方程式

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

溶媒

EtOH

反応条件

後処理

1. 1
   その他75% of the solvent were evaporated
2. 2
   workup.ADDITIONthe resulting mixture was poured into 5 ml of water
3. 3
   抽出extracted with EtOAc
4. 4
   乾燥Drying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2

実験手順

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).

出典