Hydrochloric Acid → (2E,4E,6E)-7-(3-Ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-6-fluoro-3-methylnona-2,4,6-trienoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl (2E,4E,6E)-7-(3-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-6-fluoro-3-methylnona-2,4,6-trienoate (Compound 1, 3.55 g, 8.02 mmol) in ethanol (60 mL) was treated with 2 N aqueous potassium hydroxide (20 mL), and the solution was stirred at 60° C. overnight. The solution was cooled to room temperature, and acidified with 1 N HCl, and the products were extracted three times with ethyl acetate. The combined organic layers were washed with water, brine and dried over magnesium sulfate. The solution was filtered through a sintered glass funnel containing a bed of silica gel about 1 inch thick using ethyl acetate as the eluent. The solvent was removed in vacuo, and the residue was recrystalized form acetonitrile to give the title compound.

Provenance & Evidence