Azobisisobutyronitrile → HCID 14820509, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-hydroxy-6-allyl-2,3-dihydrobenzothiophene (125 mg, 0.65 mmole) in 0.5 mL thiophenol was added 28 mg AIBN. The reaction mixture was purged with nitrogen and heated to 90° C. for 3 hours. TLC analysis (90/10 hexane/EtOAc) showed the reaction to be complete. The reaction mixture was diluted with 25 mL saturated sodium bicarbonate and extracted 3×25 mL EtOAc. The combined organics were washed with sodium bicarbonate (2×25 mL), H2O (1×25 mL) and brine (1×25 mL). Drying over Na2SO4, filtration and concentration afforded 568 mg crude product as an oil. Purification by flash chromatography (90/10, hexane/EtOAc) 126 mg (64%) pure product NMR 287 MS181.

Provenance & Evidence