Iodine → HCID 68175843, compound

Participants

Reaction Steps

Dess-Martin periodinane (46 mg, 0.109 mmol) was added to a stirred solution of 9b (40 mg, 0.073 mmol) in DCM (0.73 mL) at 0° C. After 2 h, the reaction was quenched by addition of saturated aqueous sodium thiosulfate and extracted with DCM. The combined organics were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford crude residue that was dissolved in DCM (1 mL) and added dropwise to a stirred solution in which triphenylphosphine (172 mg, 0.657 mmol), followed by triethylamine (31 μL, 0.220 mmol), had been added to iodine (28 mg, 0.110 mmol) in DCM (1 mL) at 0° C. The resulting mixture was warmed to rt, and after 1 h, quenched with saturated aqueous sodium thiosulfate. The mixture was extracted with ethyl acetate, and the combined organics were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford crude residue that was purified by flash chromatography on silica gel (gradient elution; 0%-50% EtOAc/hexanes as eluent) to afford the title compound 9c. m/z (ES) 528 (MH)+.

Provenance & Evidence