4,5-Dihydro-4,4-dimethyl-2-(3-pyridyl)oxazole → HCID 178428961, compound

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Reaction Steps

To a cooled (-78° C.) solution of 3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine [Hauck A. E., et al., J. Chem. Soc. Perkin I 1980:2070-2076] (140.0 g, 0.79 mol) in 500 mL dry tetrahydrofuran (THF), phenyllithium (1.42 mol, 1.8 eq) is added under a nitrogen atmosphere until gas chromatography (GC) analysis indicates no more starting material is present. The reaction mixture is stirred for 10 minutes and then quenched with 500 mL water at -78° C. After warming the reaction mixture to room temperature with a water bath, 700 mLof diethyl ether is added to the mixture. The resulting solid is filtered, rinsed once with chilled methanol, and then dried at 40° C. in a vacuum oven overnight to yield 166.6 g (0.65 mol) of 1,4-dihydro-3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-4-phenylpyridine.

Provenance & Evidence