1,2-Dimethoxyethane → HCID 59192526, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (3-bromo-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (XIIIb, 78 mg, 0.22 mmol), phenylboronic acid (55.3 mg, 0.44 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (24.1 mg, 0.033 mmol), and cesium carbonate (144.8 mg, 0.44 mmol) was added dimethoxyethane (2 mL) at room temperature under nitrogen. The resulting brown reaction mixture was heated at 95° C. for 15 h. Then, the reaction mixture was cooled to room temperature, and diluted with water (20 mL) and ethyl acetate (20 mL). The aqueous layer was separated and extracted with ethyl acetate (20 mL), and the combined organic extracts were washed with water (50 mL) and brine solution (50 mL), then dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the colored residue. Chromatography using an ISCO (12 g) column, (gradient elution with 2-25% ethyl acetate in hexanes) afforded (5-oxo-3-phenyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (54 mg, 70%) as a white solid: ES(+)-HRMS m/e calcd. for C22H24O4 (M+Na)+375.1567, obsd. 375.1567.

Provenance & Evidence