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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1271301Generated: October 25, 2026

2-(4-Pentynyloxy)tetrahydro-2H-pyran → 5,6-Diphenyl-2-[5-(2-tetrahydropyranyloxy)-1-pentyn-1-yl]pyrazine

https://huagongshe.com/reaction/1271301

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-(4-Pentynyloxy)tetrahydro-2H-pyranHCID 357816—
Reactant5-Chloro-2,3-DiphenylpyrazineHCID 3654493—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418476HCID 178418476—
SolventTriethylamineHCID 8471—
Product5,6-Diphenyl-2-[5-(2-tetrahydropyranyloxy)-1-pentyn-1-yl]pyrazineHCID 2293195575.8%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution of 1.58 g of 2-chloro-5,6-diphenylpyrazine in 10 ml of triethylamine, 1.20 g of 5-(2-tetrahydropyranyloxy)-1-pentyne, 208 mg of dichlorobis(triphenylphosphine)palladium (II) and 56 mg of copper (I) iodide were added, followed by stirring under an argon atmosphere at 80° C. for 8 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in diethyl ether, and then the insoluble matter was removed by filtration through celite. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography to obtain 1.79 g of the desired compound as a brown oily substance.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07205302B2
Source datasetuspto-grants-2007_04
ORD IDord-30c9cb5a484e4641a505c92c2d64f0e7
Source noteuspto-grants-2007_04