Chlorotrimethylsilane → HCID 59633933, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of zinc (3.0 g) and lithium chloride (1.5 g) in THF (25 mL) were added dibromoethane (0.30 mL) and chlorotrimethylsilane (0.44 mL) at 70° C. under argon atmosphere. The mixture was stirred at 70° C. for 10 min. A solution of 1-Boc-3-iodoazetidine (9.8 g) in THF (10 mL) was added dropwise to the mixture at RT. The mixture was stirred at RT for 1 hr. To the mixture were added a solution of 1-(4-cyclopropylbenzyloxy)-4-iodo-2-methoxybenzene (5.3 g) prepared in (3) in THF (15 mL) and bis(triphenylphosphine)palladium (II) dichloride (0.49 g). The reaction mixture was stirred at RT for 3 hr. The reaction mixture was quenched with saturated aqueous NH4C1 and extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1 to 4/1) to give the title compound.

Provenance & Evidence