Hydrochloric Acid → HCID 68827228, compound

Participants

Reaction Conditions

Reaction Steps

Aqueous KOH (0.3 g in 250 mL water) was added to 4-fluoro-benzaldehyde Compound 12a (4.82 g, 38.9 mmol) and tetrahydro-4H-thiopyran-4-one Compound 1a (4.5 g, 38.8 mmol), and the mixture was heated to about 65° C. for 24 hrs, then cooled to r.t. and stirred for 2 hrs. The mixture was acidified to pH 7 with 1.0N HCl (2 mL) and diluted with EtOAc (200 mL). The organic layer was separated, washed with brine and dried with anhydrous Na2SO4, then filtered and concentrated to provide a crude product, which was purified by silica gel column (eluted with 8% EtOAc in hexane) to give 3-(4-fluoro-benzylidene)-tetrahydro-4H-thiopyran-4-one Compound 12b (4.8 g, 48.5%) as a white solid.

Provenance & Evidence