Tetrabutylammonium Fluoride → 5-(4-Chloro-phenyl)-2-ethynyl-pyridine

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Reaction Steps

43.66 g (156.0 mmol) of TBAF are added at RT to a solution of 46.50 g (142.0 mmol) of 2-[(tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)pyridine in 1 L of DCM and the mixture is stirred for 2 hours. The organic phase is washed with water, dried over sodium sulfate, and evaporated down in vacuo. The residue is stirred with DIPE, and the precipitate is filtered off and washed with PE. Yield: 26.0 g (86% of theoretical);C13H8CIN (M=213.662); calc.: molpeak (M+H)+: 214/216 (Cl); found: molpeak (M+H)+: 214/216 (Cl); Rf value: 0.30 (silica gel, Cyc/EtOAc 4:1).

Provenance & Evidence