Maleic Anhydride → (S)-1-[2-(Acetyloxy)-1-phenylethyl]-2,5-dihydro-1H-pyrrol-2,5-dione

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Reaction Steps

Maleic anhydride (358 mg, 3.65 mM) was added to (S)-(+)-2-phenylglycinol (500 mg, 3.65 mM) dissolved in 5 ml THF stirred under Ar. A precipitate formed immediately but redissolved after 1 hr. The mixture was stirred overnight. TLC (silica gel, EtOAc/HOAc 95:5) showed two spots, the product Rf 0.34, and a lower Rf spot, Rf 0.09. The THF was evaporated, and the residue was dissolved in 6 ml hot CH2Cl2. Crystals formed almost immediately in the hot mixture which was let stand at 5° for 2 hrs. The crystals were filtered, washed with cold CH2Cl2, and dried under vacuum to give the title compound: 600 mg (70%), mp. 131°-2°. ##STR48##

Provenance & Evidence