4-Hydroxybenzyl Alcohol → 4-(4-Allyldimethylsilylbenzyloxy)benzyl Alcohol

Participants

Reaction Steps

A solution of 4-allyldimethylsilylbenzyl bromide (4 Scheme 13, 2.7 g, 10 mmol), 4-hydroxybenzyl alcohol (12.5 g, 10 mmol), tetrabutylammonium iodide (100 mg) and powdered K2CO3 (2.1 g, 15 mmol) in acetone (60 mL) was stirred at 60° C. for 22 h. The precipitated sol was filtered and the filtrate was concentrated. The crude oil was purified by column chromatography (1:3 ethyl acetate/hexanes) to afford a colorless oil (2.9 g, 94%); 1H NMR (300 MHz, CDCl3) δ 0.37 (s, 6 H), 1.84 (d, J=6.30 Hz, 2 H), 2.72 (s, OH, 1 H), 4.58 (s, 2 H), 4.93 (s, 1 H), 4.97 (m, 2 H), 5.09 (s, 1 H), 5.86 (ddt, J=16.80 Hz, 10.50, 8.10 Hz, 1 H), 7.01 (d, J=8.40 Hz, 2 H), 7.30 (d, J=8.40 Hz, 2 H), 7.48 (d, J=7.90 Hz, 2 H), 7.61 (d, J=7.90 Hz, 2 H); 13C NMR (75 MHz, CDCl3) −3.1 (2 C), 24.0, 65.0, 70.2, 113.9, 115.2 (2 C), 127.1 (2 C), 128.9 (2 C), 133.8, 134.2 (2 C), 134.8, 138.1, 138.7, 158.6. HRMS (EI) calcd for C19H24O2Si 312.1545, found 312.1547.

Provenance & Evidence