Sodium Iodide → HCID 15078340, compound

Participants

Reaction Steps

To a stirred slurry of 108 mg of 50% sodium hydride-mineral oil dispersion (prewashed with hexane) in 1 ml of anhydrous N,N-dimethylformamide was added a solution of 268 mg of racemic-3,4-dihydro-7-hydroxy-2-methyl-3-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester in 3 ml of dry N,N-dimethylformamide at room temperature, over a 1 minute period. After being stirred for 30 minutes at room temperature, the mixture was treated dropwise with a solution of 313 mg of 4'-(3-bromopropoxy)-2'-hydroxy-3'-n-propylacetophenone in 3 ml of dry N,N-dimethylformamide. Sodium iodide (0.3 g) was added and the mixture was stirred at room temperature for 2.5 hours before being quenched with 1 ml of water. After 30 minutes, 0.3 g of lithium hydroxide monohydrate and 1 ml of water were added and stirring was continued for 3 hours. The mixture was acidified to pH 1 with 1N hydrochloric acid and worked-up with ether in the usual manner. The orange oily product (0.7 g) was chromatographed on 50 g of silica gel. Elution with 4:1 toluene-ethyl acetate gave 310 mg (69.1%) of racemic-7-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3,4-dihydro-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid as a viscous yellow oil after drying at 60° C. under high vacuum.

Provenance & Evidence