Triacetoxyperiodinane → 1-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile

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Reaction Steps

To a room temperature solution of 1-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile (1.6 g, 7 mmol, 1 equiv.) in 50 mL of CH2Cl2 was added Dess-Martin periodinane (3.6 g, 8.3 mmol, 1.2 equiv). After 3 hours, the reaction was diluted with CH2Cl2 and made basic with saturated NaHCO3. The organic layer was separated and the aqueous extracted with CH2Cl2. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc-hexanes (0-15% gradient) to provide 1-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile which was used without further purification.

Provenance & Evidence