1,2-Dimethoxyethane → 18-(p-Iodophenyl)octadecyl acetate

Participants

Reaction Conditions

Reaction Steps

Zinc powder (340 mg, 5.21 mmol) was dried in a 25-ml flask under high vacuum at 70° C. for 30 min, then DMA (1 ml) and 12 (44 mg, 0.17 mmol) were added. After 10 min, solution or 17-acetoxy-heptadecyl iodide (1.473 g, 3.47 mmol) in DMA (5 ml) was added. Reaction mixture was stirred at 60-70° C. for 10 h, cooled to room temperature and solution of the organozinc reagent was transferred via cannula into 25 ml round bottom flask equipped with the stir bar. The flask with organozinc solution 41 was immersed into an ice bath. In a 10-ml round bottom flask, NiCl2.glyme (76 mg, 0.347 mmol) and (R)-(i-Pr)-Pybox (or (S)-(i-Pr)-Pybox) (136 mg, 0.45 mmol) were dissolved in DMA (2 ml), then solution of p-iodobenzyl bromide (1.55 g, 5.21 mmol) in DMA (3 ml) was added. The solution of NiCl2-Pybox catalyst and p-iodobenzyl bromide was added to the solution of organozinc reagent 41 at 0° C. within 2-3 min. Reaction mixture was stirred at 0° C. for 30 min and at room temperature for 12-24 h. The reaction was quenched by addition of aqueous NH4Cl, extracted with EtOAc, extract was dried over Na2SO4 and evaporated. The crude product was purified by silica gel chromatography in hexane-ether (98:2) to give the product (1.58 g, 88%).

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