Methyl iodide → (3-Methoxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester

Participants

Reaction Steps

To a suspension of (3-hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (XXX, 78 mg, 0.27 mmol) and potassium carbonate (111 mg, 0.8 mmol) in acetone (4 mL) and DMF (2 mL) was added iodomethane (114 mg, 0.8 mmol) at room temperature under nitrogen. The resulting red-brown suspension was heated at reflux for 2 days. The reaction mixture was then cooled to room temperature and diluted with water (10 mL) and brine (10 mL). The resulting 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 using ISCO (40 g) column chromatography (gradient elution with 5-40% ethyl acetate in hexanes) to obtain (3-methoxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (76 mg, 94%) as a light yellow solid: ES(+)-HRMS m/e calcd. for C17H22O5 (M+H)+307.1540, obsd. 307.1540.

Provenance & Evidence