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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1916548Generated: November 1, 2026

Water → 5-(4-Chloro-phenyl)-2-ethynyl-pyridine

https://huagongshe.com/reaction/1916548

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant5-(4-Chlorophenyl)-2-trimethylsilanylethynylpyridineHCID 67363611—
SolventDichloromethaneHCID 6344—
Product5-(4-Chloro-phenyl)-2-ethynyl-pyridineHCID 57845328—

Reaction Steps

Under an argon atmosphere 6.6 g (21.0 mmol) TBAF are added to a solution of 5.8 g (20.3 mmol) 5-(4-chloro-phenyl)-2-trimethylsilanylethynyl-pyridine in 200 mL DCM at 0° C. The reaction solution is stirred for 3 h, while the reaction temperature slowly rises to RT. It is added to 50 mL water and the organic phase is extracted four times with 50 mL water, dried over MgSO4 and filtered over activated charcoal. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (PE/EtOAc 1:1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618132B2
Source datasetuspto-grants-2013_12
ORD IDord-d186bbf9df2649b3aa1304bec28c4c7a
Source noteuspto-grants-2013_12