Chlorotrimethylsilane → HCID 59633969, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of zinc (20.7 g) and lithium chloride (10 g) in THF (120 mL) were added dibromoethane (2 mL) and chlorotrimethylsilane (3 mL) at 70° C. under argon atmosphere. The mixture was stirred at 70° C. for 10 min. A solution of 1-Boc-3-iodoazetidine (67 g) in THF (120 mL) was added dropwise to the mixture at RT. The reaction mixture was stirred for 1 hr. To the mixture were added a solution of 1-(4-ethylbenzyloxy)-4-iodo-2-methoxybenzene (58.1 g) prepared in (1) in THF (120 mL) and bis(triphenylphosphine)palladium (II) dichloride (0.49 g). The reaction mixture was stirred at RT for 3 hr. Saturated aqueous NH4Cl was added to the reaction mixture and the mixture was 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=4/1) to give the title compound (32.4 g, 52%).

Provenance & Evidence