Triphenylphosphine → 5-(1-Azidoethyl)-2-fluoropyridine

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Reaction Steps

To a 1-L flask kept cold in a ice bath, add triphenylphosphine (27.9 g, 106.3 mmol), 1,4-cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(24.12 g, 106.3 mmol). Add dichloromethane slowly with stirring (150 mL). To the dark solution add tetra-N-butylammonium azide (30.23 g, 106.3 mmol) slowly, followed by 1-(6-fluoro-pyridin-3-yl)-ethanol (10 g, 70.85 mmol) dissolved in dichloromethane (10 mL). Remove the flask from the ice bath and stir at room temperature for 1 hour. Remove the solvent on a rotovap and purify by normal phase chromatography 5% to 20% ethyl acetate in hexanes to obtain the product as colorless oil (7.75 g). GCMS (EI) m/z 166 M+.

Provenance & Evidence