Thionyl Chloride → HCID 178456588, compound

Participants

Reaction Conditions

Reaction Steps

To Compound 1a (578 mg, 1.46 mmol) was added thionyl chloride (5.0 mL, 68.5 mmol, 47 equivalents) and the mixture was stirred at 60° C. for 2 hours. Excess thionyl chloride was evaporated, to the resulting residue were added chloroform (10 mL) and saturated aqueous sodium hydrogen carbonate (10 mL), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was extracted with chloroform, the organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=98:2), and chloroform and methanol were added to the residue. The deposited crystals were collected by filtration to obtain the title compound (310 mg, 56%) as a white solid.

Provenance & Evidence