Carbon Dioxide → HCID 21496259, compound

Participants

Reaction Steps

A suspension of 5.0 gm (16.4 millimols) of [1-(2'-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid, m.p. 164°-165° C., in 50 ml of dry tetrahydrofuran was admixed with 2.92 gm (18.1 millimols) of carbonyldiimidazole, whereupon the acid dissolved and carbon dioxide was given off. After one hour, 1.37 gm (18.1 millimols) of glycol monomethyl ether were added, and the mixture was allowed to stand for 2 hours. For isolation of the reaction product, the mixture was evaporated, and the residue was distributed between dilute hydrochloric acid and ethyl acetate, and the organic solution was purified by chromatography on 180 gm of silicagel with cyclohexane/ethyl acetate=1/4. For further purification, the product mixture was recrystallized from cyclohexane/ethyl acetate=4/1. Yield: 3.8 gm (63.8% of theory); m.p. 65°-67° C.

Provenance & Evidence