Thionyl Chloride → 4,5-Dihydro-4,4-dimethyl-2-[4-(phenylmethoxy)phenyl]oxazole

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Reaction Steps

Thionyl chloride (11 ml, 150 mmol, 3 eq) is added to a solution of 4-(benzyloxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide ax1 (14.98 g, 50 mmol, 1 eq) in chloroform (400 ml) and the mixture is heated at reflux for 2 h. The solvent is then removed under vacuum, and the residue is dissolved into dichloromethane. The organic layer is washed with a saturated solution of aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under vacuum to give 2-[4-(benzyloxy)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole ax4 (4.3 g).

Provenance & Evidence