反応 #85593

反応方程式

3-methyl-4-nitrophenol

trifluoroethyl ether

phenolate

2,2,2-trifluoroethyl tosylate

indole

sodium hydride

→

title compound

5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid

溶媒

HMPA

反応条件

後処理

1. 1
   その他5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid was prepared
2. 2
   その他reported in Synthesis (1980) 727

実験手順

5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid was prepared following the procedure reported in Synthesis (1980) 727. 3-methyl-4-nitrophenol (Aldrich) was deprotonated with sodium hydride in HMPA, and the resulting phenolate alkylated with 2,2,2-trifluoroethyl tosylate (Aldrich). The resulting trifluoroethyl ether was then converted to the indole using the Batcho-Leimgruber protocol. Formylation and oxidation as described herein gave the title compound as an off-white solid. MS (m/e) 260.

出典