Sodium Iodide → 2-[6-[4-Acetyl-3-hydroxy-2-(3-phenylpropyl)phenoxy]hexyl]-6-[(6-methoxy-6-oxohexyl)oxy]benzenepropanoic acid methyl ester

Participants

Reaction Steps

A mixture of 0.81 g (3 mmol) of 1-[2,4-dihydroxy-3-(3-phenylpropyl)phenyl]ethanone from example 191, 1.6 g (3.29 mmol) of 2-[(6-methoxy-6-oxohexyl)oxy]-6-[6-[(methylsulfonyl)oxy]hexyl]benzenepropanoic acid methyl ester from example 156, 0.66 g (4.78 mmol) of anhydrous, granular potassium carbonate, 0.55 g (3.67 mmol) of sodium iodide, and 25 mL of acetonitrile was stirred and refluxed for 18.5 hr. The resulting thick slurry was cooled, diluted with ether, washed with water, 12% aqueous sodium bisulfite, and brine, and work-up was completed in the usual manner. Thin layer chromatographic analysis of the oily product revealed that alkylation was incomplete. Therefore, the product was dissolved in 5 mL of acetonitrile and 0.69 g (5 mmol) of anhydrous, granular potassium carbonate was added. The resulting mixture was stirred and refluxed for 24 hr before being worked-up as described above. The oily product (2.01 g) was chromatographed on 50 g of silica gel. Elution with 1:1 hexane-ether afforded 1.80 g (90.9%) of the title compound as an almost colorless oil.

Provenance & Evidence