Whitby group

To a stirred solution of ((3-ethynylbenzyl)oxy)triisopropylsilane (0.60 g, 2.08 mmol, 1 equiv.) in THF (15 mL) at -78°C was added slowly dropwise n-butyl lithium (2.5 M in hexanes, 0.97 mL, 2.50 mmol, 1.2 equiv.).  The reaction was warmed to -50 °C and HMPA (0.54 mL, 3.12 mmol, 1.5 equiv.).  The reaction was stirred for 20 minutes at this temperature before being allowed to warm to room temperature and stirred for 16 hours.

The reaction was quenched with ammonium chloride solution (sat. aq., 10 mL) and the product was extracted into diethyl ether (3 x 10 mL).  The diethyl ether washes were combined and washed with water (3 x 30 mL) and brine (30 mL) before being dried over magnesium sulphate, filtered and concentrated under reduced pressure.

The product was purified by column chromatography (silica gel, 1 % diethyl ether in hexane) to yield the product (0.58 g, 1.63 mmol, 78 %).