Phenylacetic Acid → HCID 19969600, compound

Participants

Reaction Steps

A 2.5M hexane solution of butyl lithium (180 ml) was added to an ice-cooled solution of phenylacetic acid (20 g), hexamethylphosphoramide (25.6 ml) and tetrahydrofuran (260 ml). The reaction mixture was stirred to room temperature, then cooled back to 0° C. A solution of 2-(3-chloropropyl)-1,3-dioxolane in THF (20 ml) was added dropwise and the mixture was stirred to room temperature overnight. The reaction was cooled back down to 0° C. then butyl lithium (60 ml of a 2.5M hexane solution) was added dropwise followed by picolyl chloride (0.147 mol) in THF (40 ml). The ice-bath was removed and the reaction was stirred at room temperature for 3 days. The reaction mixture was quenched with half-saturated aqueous NH4Cl. Ethyl acetate and chloroform were added to dissolve the solids. The aqueous layer was neutralized with 1N HCl and extracted with chloroform. The combined organic layers were dried (MgSO4) and concentrated to give a solid which was washed with ether to give the subtitle compound (28.1 g).

Provenance & Evidence