반응 #77795

반응 방정식

Et2O

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

N-ethyldiisopropylamine

methanesulfonyl chloride

→

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

수율 62.7%

용매

CH2Cl2

반응 조건

후처리

1. 1
   세척washed with 0.5 M HCl
2. 2
   건조Drying of the organic layer with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2

실험 절차

A solution of 120 mg (0.321 mmol) 6-Fluoro-5-(5-hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester and 0.164 ml (0.96 mmol) N-ethyldiisopropylamine in 2 ml CH2Cl2 was treated with 0.03 ml (0.385 mmol) of methanesulfonyl chloride and stirred at room temperature for 1 hour. The mixture was poured into Et2O and washed with 0.5 M HCl. Drying of the organic layer with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2 gave 91 mg (61%) of 6-Fluoro-5-(5-methanesulfonyloxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as a colorless oil, MS: 452 (MH+, 1Cl).

출처