Hydrochloric Acid → HCID 89904800, compound

Participants

Reaction Steps

To a tetrahydrofuran (140 mL) solution of the compound 4 (34.9 g) was added a 2M aqueous sodium hydroxide solution (140 mL), and the mixture was stirred at room temperature for 18 hours and then at 50° C. for 3 hours. The mixture was cooled to −4° C. in an ice-methanol bath, and to the reaction mixture was then added dropwise 2 M hydrochloric acid (111 mL) over 12 minutes while the mixture was kept at 2° C. or lower (pH 5 to 6). The cooling bath was changed to an ice bath, and to the reaction mixture were added sodium hydrogen carbonate (28.5 g) and iodine (17.5 g), and the mixture was stirred. After 2 hours, iodine (34.2 g) was added, the mixture was further stirred for 2.5 hours, and a 5% aqueous sodium thiosulfate solution (1380 mL) was then added. When the color of iodine mostly disappeared, ethyl acetate (600 mL) was added, the mixture was stirred, and the two layers were separated. The organic layer was washed with water (150 mL) and a saturated saline (150 mL), dried with anhydrous sodium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→5:6) to obtain titled compounds having the following physical property values (low polar compound 8.0 g; high polar compound 20.8 g).

Provenance & Evidence