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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 965490Generated: October 23, 2026

Tri-o-tolylphosphine → Ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8-(phenylthio)naphthalenyl)ethenyl]benzoate

https://huagongshe.com/en/reaction/965490

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTri-o-tolylphosphineHCID 80271—
ReactantEthyl 4-vinylbenzoateHCID 10866858—
Reactant4,4-Dimethyl-7-bromo-1-phenylthio-3,4-dihydronaphthaleneHCID 15896018—
Catalystpalladium(II) acetateHCID 167845—
SolventTriethylamineHCID 8471—
ProductEthyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8-(phenylthio)naphthalenyl)ethenyl]benzoateHCID 19695074—

Reaction Conditions

Temperature90 °C

Reaction Steps

To a degassed solution of 0.35 g (1.0 mmol) of 2-bromo-5,6-dihydro-5,5-dimethyl-8-(phenylthio)-naphthalene (Compound A35) and 0.34 g (1.9 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine, was added 0.066 g (0.2 mmol) of tri-o-tolylphosphine and then 0.025 g (0.1 mmol) of palladium(II) acetate. The reaction was heated at 90° C. for 2.25 h. The reaction was concentrated in vacuo. The residue was purified by flash chromatography (silica, 5% ethyl acetate in hexane), followed by recrystallization using EtOH to afford the title compound as white crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05773594
Source datasetuspto-grants-1998_06
ORD IDord-b8ee9d94292e43ad9d037d4aaa1e830e
Source noteuspto-grants-1998_06