Imidazole → 5-Benzyloxyethyl-2,2-dimethyl-5-(t-butyldiphenylsiloxymethyl)-1,3-dioxane

Participants

Reaction Conditions

Reaction Steps

459 mg (1.64 mmol equivalents) of 5-benzyloxyethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane was dissolved in 8 mL of dimethylformamide, 197 mg (3.20 mmol equivalents) of imidazole and 0.51 mL (1.92 mmol equivalents) of t-butyldiphenylchlorosilane were added thereto, and the mixture was stirred at room temperature (25° C.) for 22 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added thereto, and the mixture was extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate, and subsequently concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=20/1) to give 570 mg (1.56 mmol equivalents) of 5-benzyloxyethyl-2,2-dimethyl-5-(t-butyldiphenylsiloxymethyl)-1,3-dioxane.

Provenance & Evidence