Water → HCID 60167282, compound

Participants

Reaction Conditions

Reaction Steps

Naphthol 7 (3.20 g, 11.0 mmol) was dissolved in anhydrous DMF (78 mL). K2CO3 (3.05 g, 22.0 mmol), benzyl bromide (1.59 mL, 13.2 mmol), and Bu4NI (163 mg, 0.440 mmol) were added. The solution was stirred at 25° C. for 16 h. The reaction mixture was poured into H2O and extracted with ethyl acetate (3×). The organic extracts were combined, dried over Na2SO4, and concentrated under reduced pressure. The solid was recrystallized with 5% EtOAc/hexanes and the mother liquor was further purified by flash chromatography (SiO2, 6×15 cm, 10-20% EtOAc/hexanes gradient elution) affording additional 8 (3.30 g combined, 77%) as a brown crystalline solid. 1H NMR (CDCl3 500 MHz) δ 8.17 (s, 1H), 7.87 (d, J=7.5 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.61 (d, J=7.5 Hz, 2H), 7.57 (s, 1H), 7.40 (t, J=7.5 Hz, 2H), 7.35-7.32 (m, 1H), 7.29 (t, J=7.5 Hz, 1H), 5.30 (s, 2H), 4.43 (q, J=7.0 Hz, 2H), 1.44 (t, J=7.0 Hz, 3H). 13C NMR (CDCl3, 125 MHz) δ 166.0, 154.5, 136.1, 136.0, 135.0, 129.3, 128.3, 128.0 (2C), 127.8, 126.8, 125.8, 124.1, 116.7, 106.9, 71.2, 61.1. IR (film) νmax 2980, 1712, 1413, 1236 cm−1. ESI-TOF HRMS m/z 385.0433 (M+H+, C20H17BrO3 requires 385.0434).

Provenance & Evidence