Methanol → [2-Methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-phenyl-acetic acid methyl ester

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Reaction Conditions

Reaction Steps

A solution of 0.14 g (0.34 mmol) 2-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indole (example 51.2) in 1.5 mL of methanol was treated with 0.028 g (0.34 mmol) of sodium actetate and 0.053 mL (0.34 mmol) of α-bromophenyl methyl acetate. The mixture was stirred at 100° C. in a pressure tube for 10 hrs and then distributed between Et2O and a saturated aqueous solution of NH4Cl. The combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-heptane/EtOAc 4:1 yielded 170 mg of [2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-phenyl-acetic acid methyl ester, colourless viscous oil, MS: 448 (MH+).

Provenance & Evidence