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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 480477Generated: October 29, 2026

Toluene → HCID 178474043, compound

https://huagongshe.com/reaction/480477

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantBenzophenone imineHCID 136809—
ReactantHCID 22018349HCID 22018349—
ReactantSodium t-butoxideHCID 23676156—
CatalystBinap, (A+-)-HCID 634876—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventEthyl AcetateHCID 8857—
ProductHCID 178474043HCID 178474043—

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 1-(6-bromo-naphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (14.0 g), benzophenone imine (5.18 g), tris(dibenzylideneacetone)dipalladium (440 mg), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (872 mg) and sodium t-butoxide (5.72 g) in toluene (140 ml) was heated at 80° C. for 18 h under argon atmosphere. After cooling, the mixture was diluted with ethyl acetate, filtered with celite pad. The filtrate was concentrated and the residue was chromatographed on silica gel (eluent; hexane:THF=1:1) followed by crystallization from hexane-THF (4:1) to give yellow titled compound (14.3 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06649643B1
Source datasetuspto-grants-2003_11
ORD IDord-234d976244c044abb824a619305a0563
Source noteuspto-grants-2003_11