Sodium Carbonate → HCID 68539388, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube containing 2-bromo-3-(1-methylethyl)-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}naphthalene (70) (0.24 g, 0.71 mmol), phenyl boronic acid (0.18 g, 1.41 mmol), Pd(PPh3)4 (82 mg, 0.07 mmol), 2 M Na2CO3 (5 mL) and DME (5 mL) was heated at 160° C. for 20 min. Cooled to room temperature, the mixture was extracted with ether (2×50 mL). The organic extracts were combined and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a yellow oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (25:1) to give 0.23 g (97%) of compound 71 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.16 (d, J=6.8 Hz, 6H), 2.92 (sept, J=6.8 Hz, 1H), 3.06 (s, 3H), 3.93 (s, 3H), 4.71 (s, 2H), 7.08-7.15 (m, 2H), 7.30-7.40 (m, 3H), 7.40-7.46 (m, 2H), 7.52 (s, 1H), 8.01 (d, J=9.0 Hz, 1H).

Provenance & Evidence