Sodium Bicarbonate → HCID 22033010, compound

Participants

Reaction Steps

(3RS,4RS)-7-Methoxymethoxy-3-[4-(methoxymethoxy)phenyl]-3-methyl-4-{3-{4-[2-(4,4,5,5,5-pentafluoropentylthio)ethoxy]phenoxy}propyl}thiochroman (9) prepared in Step 7 (144 mg, 0.2 mmol) was dissolved in hydrochloric acid/methanol (1 ml) and tetrahydrofuran (0.1 ml), which was then stirred at room temperature for 4 days. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the resulting mixture was extracted with ethyl acetate and chloroform. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and subjected to silica gel column chromatography to give (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-{3-{4-[2-(4,4,5,5,5-pentafluoropentylthio)ethoxy]phenoxy}propyl}thiochroman (11) (110 mg, yield 87%) as a yellow oily substance.

Provenance & Evidence