Benzoyl chloride → ((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methyl benzoate

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Reaction Steps

Benzoyl chloride (1.92 mL, 0.0166 mol) was added to a solution of ((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methanol (from step 8) (2.72 g, 0.0138 mol) in 20 mL of anhydrous pyridine at 0° C. To this mixture 5 mol % of DMAP was added and stirred at room temperature for 3 h. Pyridine was removed under vacuum; the residue was diluted with ethyl acetate and washed with 1N HCl, saturated NaHCO3 and brine. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The compound was purified via column chromatography using hexane and ethyl acetate as a gradient mixture to give 4.1 g of the title compound (97% yield).

Provenance & Evidence