Sodium hydride → HCID 66971860, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottom flask containing the product of Step 4 for the preparation of Example 1 (2.00 g, 4.80 mmol) was fitted with a stirbar and septa and flushed with nitrogen. Tetrahydrofuran (20 mL) was added, giving a solution that was cooled to 0° C. Sodium hydride (0.781 g, 60%/oil, 19.5 mmol) was added, and the reaction was stirred for 30 minutes. Trifluoromethanesulfonic acid-2,2,2-trifluoroethyl ester (2.26 g, 9.74 mmol) was then added, and stirring was continued with gradual warming to room temperature. After 18 hours, the reaction mixture was poured into ethyl acetate (75 mL) and washed first with 1:1 H2O:saturated aqueous NaHCO3 solution (2×30 mL), then with saturated aqueous NaCl solution (20 mL). The aqueous wash layers were combined and extracted with ethyl acetate (30 mL). The ethyl acetate layers were then combined, dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via flash chromatography on silica gel (5% to 15% ethyl acetate/hexanes linear gradient) to give the desired product.

Provenance & Evidence