Tetrabutylammonium Fluoride → (3-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester

Participants

Reaction Steps

To a solution of (5-oxo-3-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (XXIX, 140 mg, 0.33 mmol) in tetrahydrofuran (5 mL) was added a 1.0 M solution of tetrabutylammonium fluoride (660 μL, 0.66 mmol) in tetrahydrofuran at room temperature under nitrogen. The resulting light yellow solution was stirred for 5 h at room temperature, and then diluted with water (10 mL) and 1.0N hydrochloric acid (5 mL). The mixture was extracted with ethyl acetate (2×35 mL). The combined organic extracts were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by ISCO (40 g) column chromatography (gradient elution with 5-50% ethyl acetate in hexanes) to provide (3-hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (82 mg, 85%) as a yellow solid: ES(+)-HRMS m/e calcd. for C16H20O5 (M+H)+293.1384, obsd. 293.1383.

Provenance & Evidence