Nitrogen → HCID 22261177, compound

Participants

Reaction Steps

2-(5-Methyl-2-phenyloxazol-4-yl)ethanol [Hulin, et al., J. Med. Chem. (1992) 35(10), 1853-64] (7.42 g, 36.0 mmol), 4-benzyloxyphenol (7.3 g, 36.0 mmol) and triphenylphosphine (9.57 g, 36.0 mmol) were dissolved in anhydrous THF (500 mL) and treated with dropwise addition of diisopropyl azodicarboxylate (7.18 mL, 36.0 mmol). The reaction mixture was stirred at 20° C. for 18 h under a positive-pressure atmosphere of N2. The reaction was partitioned between EtOAc (100 mL) and 0.1 N NaOH (100 mL), and the organic phase washed with water (100 mL) and brine (100 mL). The organic layer was dried with Na2SO4 and concentrated to a residue which was purified by gradient column chromatography (silica column, 100% hexanes to 20% EtOAc/hexanes) to provide a white solid (10.5 g, 76%). Rf=0.3 (10% EtOAc/hexanes) 1H NMR (250 MHz, DMSO-d6) δ 7.86 (d, 2H), 7.41-7.48 (m, 3H), 7.22-7.38 (m, 5H), 6.86 (d, 2H), 6.80 (d, 2H), 4.97 (s, 2H), 4.07 (t, 2H), 2.84 (t, 2H), 2.30 (s, 3H).

Provenance & Evidence