Boron trifluoride etherate → 1,1'-[Oxybis(methylene)]bis(4-methoxybenzene)

Participants

Reaction Steps

To a stirred 0° C. solution of the alcohol (755 mg, 1.22 mmol) and p-methoxybenzyltrichloroacetimidate (3.446 g, 12.2 mmol) in CH2Cl2 (120 mL) at 0° C. was added a 0.1 M solution of BF3.OEt2 in CH2Cl2 (50 μL). The resulting orange solution was stirred for 10 min, at which time TLC showed no remaining starting material. Saturated aqueous NaHCO3 (40 mL) was added, and after vigorous mixing the separated organic phase was dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica gel (hexanes/ethyl acetate; 5:1) to give the p-methoxybenzyl ether (866 mg, 1.17 mmol, 96% yield) as a clear oil.

Provenance & Evidence