1-Naphthalenesulfonyl chloride → 1-Naphthalenesulfonic acid 3-benzyloxy-5-methylphenyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 3-benzyloxy-5-methylphenol (600 mg, 3.0 mmol), as prepared in step a of Example 3, in methylene chloride (15 mL) at 0° C. was treated with N,N-diisopropylethylamine (0.5 mL) and 1-naphthalenesulfonyl chloride (670 mg, 3.0 mmol). The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 2 h. The reaction mixture was diluted with methylene chloride (200 mL) and water (50 mL). The organic extract was washed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (1:1 hexane:methylene chloride) to give the title compound as a colorless liquid (1.05 g, 87%). 1H-NMR (300 MHz, CDCl3) δ 2.16 (s, 3H), 4.73 (s, 2H), 6.23 (t, 1H), 6.37 (dd, 1H), 6.61 (dd, 1H), 7.28 (m, 5H), 7.48 (t, 1H), 7.67 (t, 1H), 7.77 (t, 1H), 7.97 (t, 1H), 8.12 (dt, 2H), 8.19 (dd, 1H).

Provenance & Evidence