Water → (RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester

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Reaction Steps

(RS)-[4-(tert-Butyl-diphenyl-silanyloxy)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester (6.85 g) was dissolved in THF (135 ml) and a 1 M TBAF sol. in THF (15.1 ml) was added. After 3 h the reaction mixture was poured on AcOEt (300 ml) and H2O (300 ml). The aqueous layer was extracted with two more portions of AcOEt (100 ml). The combined organic layers were washed with brine and dried (MgSO4) and the solvent was evaporated. Crystallization from ice cold CH2Cl2 afforded 3.08 g (86%) of (RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester. White crystals. MS 258.9 ([M−H]+).

Provenance & Evidence