Sodium Iodide → HCID 58591566, compound

Participants

Reaction Steps

To a solution of NaI (2.29 g, 15.4 mmol) in acetonitrile (45 mL) at room temperature, trimethylsilyl chloride (1.96 mL, 15.4 mmol) was added and the mixture was stirred for 5 min. 1-[2-(2-benzyloxy-ethyl)-benzo[b]thiophen-3-yl]-1-pyridin-2-yl-ethanol (2 g, 5.14 mmol) was added and the mixture was refluxed for 4 hours. An additional aliquot of trimethylsilyl chloride (2.6 mL, 20.5 mmol) and NaI (3.06 g, 20.6 mmol) was added and refluxing was continued for another 6 hours. Sat. NaHCO3 and EtOAc were added and the organic layer was separated. After extraction of the aqueous layers with EtOAc, the combined organic layers were dried (Na2SO4) and concentrated. Silica gel column chromatography (eluent: hexanes up to EtOAc/hexanes=1/1) afforded 2-[3-(1-pyridin-2-yl-ethyl)-benzo[b]thiophen-2-yl]-ethanol in 20% yield.

Provenance & Evidence