Tetrahydrofuran → HCID 86702582, compound

Participants

Reaction Steps

An anhydrous tetrahydrofuran (482 mL) solution of the compound 3 (79.6 g) and triphenylphosphine (57.6 g) was cooled to around −40° C. in a dry ice-methanol bath. To this solution was added acetic acid (12.6 mL), and a 40% diethyl azodicarboxylate/toluene solution (100 mL) was then added dropwise over 15 minutes. The mixture was stirred at room temperature for 4.5 hours, the reaction mixture was then poured into water (1600 mL), a mixed solution of hexane (550 mL) and ethyl acetate (550 mL) was added, and the mixture was stirred. The two layers were separated, and the organic layer was then washed with water (540 mL) and a saturated saline (540 mL), dried with anhydrous sodium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain a titled compound (69.7 g) having the following physical property values.

Provenance & Evidence