Imidazole → 4-t-Butyl-5-[4-(t-butyldimethylsiloxy)-2-phenylbenzo[d]oxazol-6-yl]-3,3-dimethyl-2,3-dihydrofuran

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Reaction Steps

In nitrogen atmosphere at a room temperature, adding 43 mg (0.63 mmol) of imidazole and 64 mg (0.42 mmol) of TBDMSCl to 2.0 ml of DMF dissolving 102 mg (0.28 mmol) of 4-t-butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [63]), the mixture was stirred for 2 hours. The mixture was added to saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, then dried with magnesium sulfate anhydride and concentrated. The concentrate was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=7:1) to obtain 108 mg of 4-t-butyl-5-[4-(t-butyldimethylsiloxy)-2-phenylbenzo[d]oxazol-6-yl]-3,3-dimethyl-2,3-dihydrofuran (Compound [65]) as a colorless oil. Yield 80.6%

Provenance & Evidence