Tetrahydrofuran → HCID 67296116, compound

Participants

Reaction Conditions

Reaction Steps

Titanium tetraisopropoxide (3.0 mL, 10 mmol) was added to a tetrahydrofuran (20 mL) solution of 4′-fluoro-1′-acetonaphthone 0.94 mL (6.0 mmol) and (R)-(+)-tert-butyl sulfinamide (610 mg, 5.0 mmol), and the mixture was heated under reflux for one full day. The reaction mixture was cooled to −78° C., followed by addition of sodium borohydride (0.76 g, 20 mmol), and then the temperature of the mixture was gradually raised to room temperature. Methanol (5 mL) and then water (20 mL) were added to the mixture under ice-cooling conditions, and the solid matter generated was filtered. The oil obtained was extracted with methylene chloride (20 mL), the organic phase was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography (ethyl acetate/hexane:67/33) to give the title compound (527 mg, 45%).

Provenance & Evidence