HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 5-(4-Chloro-phenyl)-2-ethynyl-pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | 5-(4-Chlorophenyl)-2-trimethylsilanylethynylpyridine | HCID 67363611 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-(4-Chloro-phenyl)-2-ethynyl-pyridine | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618132B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-d186bbf9df2649b3aa1304bec28c4c7a |
| Source note | uspto-grants-2013_12 |