Potassium Carbonate → 8-(4-Methoxyphenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Participants

Reaction Conditions

Reaction Steps

A flask was charged with (4-methoxyphenyl)boronic acid (515 mg, 3.39 mmol), 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (780 mg, 2.71 mmol), 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (35 mg, 0.054 mmol), 1M K2CO3 (10 mL, 10 mmol), and THF (10 mL). The reaction was degassed with N2 and heated to 50° C. for 16 hours. The reaction was cooled to room temperature and diluted with EtOAc (100 mL). The mixture was washed with water (2×25 mL) and brine (2×25 mL), and the organic layer was dried (Na2SO4), filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 40% EtOAc/hexanes) afforded 8-(4-methoxyphenyl)-1,4-dioxaspiro[4.5]dec-7-ene. Rf=0.20 (25% EtOAc/hexanes). 1H NMR (500 MHz, CDCl3): δ 7.31-7.34 (m, 2H), 6.82-6.85 (m, 2H), 5.90 (m, 1H), 4.02 (s, 4H), 3.80 (s, 3H), 2.62-2.66 (m, 2H), 2.45-2.46 (m, 2H), 1.92 (t, J=6.5 Hz, 2H).

Provenance & Evidence