Sodium borohydride → HCID 86657644, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of NaBH4 (93.1 mg) in EtOH (15 mL) was added dropwise a solution of 7-{[2,4-bis(trifluoromethyl)benzyl]oxy}-2,3-dihydro-4H-thiochromen-4-one (1.0 g) in EtOH (5 mL) at 0° C. The reaction mixture was warmed to 25° C., followed by stirring for 3 hours. The reaction liquid was concentrated under reduced pressure and to the residue were added DCM (20 mL) and then saturated aqueous NH4Cl (30 mL) at 0° C., followed by stirring for 1 hour and extracting with DCM three times (30 mL×3). The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 60:40) to obtain 7-{[2,4-bis(trifluoromethyl)benzyl]oxy}thiochroman-4-ol (845 mg) as a white solid.

Provenance & Evidence