[2-(4-Bromo-phenyl)4-isopropyl-oxazol-5-yl]-methanol → 2-(4-Bromo-phenyl)4-isopropyl-oxazole-5-carbaldehyde

Participants

Reaction Steps

A solution of [2-(4-bromo-phenyl)-4-isopropyl-oxazol-5-yl]-methanol (17.9 g, 60.4 mmol) in CH2Cl2 (450 mL) is treated at ambient temperature with acetic acid 1,1-diacetoxy-3-oxo-1□5-ioda-2-oxa-indan-1-yl ester (39 g, 92 mmol, Dess Martin reagent). The suspension is stirred 1 h and is partitioned between 10% aqueous Na2S2O3 solution (250 mL) and CH2Cl2 (150 mL). The organic layer is washed with saturated NaHCO3 (2×250 mL), and the combined aqueous layers are back-extracted with Et2O (300 mL). The combined organic layers are dried (Na2SO4) and concentrated. The crude product is purified by silica gel flash chromatography using hexanes:ethyl acetate (6:1) to give an offwhite solid (14.4 g, 81%).

Provenance & Evidence