Dichloromethane → 3-(4-Triisopropylsilanyloxymethyl-benzoyl)-benzonitrile

Participants

Reaction Steps

A solution of 3-[hydroxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile (2.06 g, 5.21 mmol), Dess-Martin periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(H)-one) (2.7 g, 6.25 mmol), and dichloromethane (50 mL) is stirred at room temperature 24 hr. The mixture is diluted with aqueous saturated sodium hydrogen carbonate and extracted with dichloromethane (2×50 ml). The combined extracts are dried over magnesium sulfate, filtered, and concentrated. The residue is purified via silica chromatography eluting with hexanes to 8:2 hexanes:ethyl acetate to give the title compound (1.2 g, 60%) as a white solid. 1H NMR (CDCl3) δ 8.06-8.10 (m, 2H), 7.89-7.91 (m, 1H), 7.79-7.81 (m, 2H), 7.66 (t, 1H), 7.54-7.56 (m, 2H), 4.97 (s, 2H), 1.17-1.31 (m, 21H).

Provenance & Evidence