Potassium Carbonate → 8-Cyclopropyl-4,4-dimethylchroman-6-carbaldehyde

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A vial was charged with Pd(OAc)2 (2.40 mg, 10.7 μmol), XPhos (10.2 mg, 0.02 mmol), potassium carbonate (148 mg, 1.07 mmol), potassium cyclopropyltrifluoroborate (58.0 mg, 0.39 mmol) and 8-chloro-4,4-dimethyl-3,4-dihydro-2H-chromene-6-carbaldehyde (80.0 mg, 0.36 mmol). The mixture was dissolved in cyclopropylmethyl ether (2.00 mL) and water (0.20 mL) and purged with Ar. The reaction mixture was then stirred at 100° C. overnight, cooled to room temperature, and filtered through a pad of celite. The filtrate was concentrated under vacuum, and the crude residue was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes to afford the desired product as a yellow oil.

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