Ammonium Chloride → Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]-3-methylbutanoate

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Reaction Conditions

Reaction Steps

In a round bottom flask, was introduced ethyl 3-{3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]phenyl}-3-methylbutanoate (2.60 g, 5.6 mmol) and tetrahydrofuran (18 mL). The mixture was cooled to 0° C. and tetrabutylammonium fluoride (1N in THF, 8.4 mL) was added. The solution was stirred for 2 hrs and hydrolyzed with saturated aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2) to yield 1.7 g (99%) of the desired product as a yellow oil.

Provenance & Evidence