Hydrochloric Acid → HCID 131717582, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with 1.5 g (3.6 mmol) of the compound of Example 2 and 20 mL anhydrous THF. The solution was cooled to -70° C. and 3.6 mL sodium bis(trimethylsilyl)amide (1.0 M solution in THF) was added via syringe. After 5 minutes, 0.6 g (3.6 mmol) trifluoromethanesulfonyl chloride was added. After 15 minutes an additional 3.6 mL sodium bis(trimethylsilyl)amide was added followed by additional 0.6 g trifluoromethanesulfonyl chloride. After stirring one hour at -70° C., the reaction solution was poured into dilute HCl and extracted with ethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, an filtered to give 1.5 g of crude orange oil. Chromatography using 20% ethyl acetate in hexanes yielded 0.42 g of the desired product as a yellow oil, a 24% yield. nD25 1.4920.

Provenance & Evidence