반응 #85593

반응 방정식

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

용매

HMPA

반응 조건

후처리

1. 1
   기타5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid was prepared
2. 2
   기타reported in Synthesis (1980) 727

실험 절차

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.

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