Sodium Chloride → HCID 59305344, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottom dissolve 1-(4-Difluoromethoxy-phenyl)-2-[4-fluoro-3-(4-hydroxy-but-1-ynyl)-phenyl]-ethane-1,2-dione (0.670 g, 1.85 mmol) was dissolved in dichloromethane (40 mL) and chilled to −78° C. Add (Dimethylamino)sulfur trifluoride (MeDAST; 2.99 g, 22.4 mmol) was introduced via syringe injection. After 30 minutes dry-ice bath was removed. After 2 hours at ambient temperature the crude reaction was carefully poured into a 500 mL beaker containing 200 cc ice-chips and sodium bicarbonate. An attempted diethyl ether extraction with diethyl ether resulted in emulsion. Sodium chloride was added to break emulsion. Organic layer was concentrated to a residue, and loaded directly on top of an 80 gm chromatography column. Purification [YAMAZEN W-Prep 2XY using automatic gradient elution: 3% EtOAc/hexanes (hold 4 min) to 24% EtOAc (in 12 min), hold 8 minutes] afforded oil that begins to solidify as a wax 360 mg (53%).

Provenance & Evidence