Iodoethane → (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester

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Reaction Conditions

Reaction Steps

A mixture of (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-2,6-difluoro-phenyl]-hydroxy-acetic acid ethyl ester (70.8 g), Ag2O (69.7 g) and iodoethane (117 g) in Tol (700 ml) was stirred 68 h at 90° C. After filtration and evaporation of the solvent the product was separated from the remaining starting material by MPLC (Hept to Hept/AcOEt 1:9). The procedure was repeated with the recovered starting material. 62.5 g (83%) of (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester were obtained. Light yellow oil. MS 498.3 (1, M+); 441.1 (73, [M−tBu]+); 425.2 (33, [M-COOEt]+).

Provenance & Evidence