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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1765784Generated: October 30, 2026

Triethylamine → {4-[5-(Cyclopropyl-methyl-amino)-4-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-acetic acid methyl ester

https://huagongshe.com/reaction/1765784

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantEthyl AcetateHCID 8857—
ReactantMethyl 4-IodophenylacetateHCID 10378700—
Reactant5-(Cyclopropyl-methyl-amino)-2-ethynyl-8,8-dimethyl-methoxy-5,6,7,8-tetrahydro-naphthaleneHCID 21107196—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418476HCID 178418476—
SolventHexaneHCID 8058—
Product{4-[5-(Cyclopropyl-methyl-amino)-4-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-acetic acid methyl esterHCID 57424241—

Reaction Steps

Following General Procedure B and using 5-(cyclopropyl-methyl-amino)-2-ethynyl-8,8-dimethyl-methoxy-5,6,7,8-tetrahydro-naphthalene (Intermediate 81, 0.065 g, 0.23 mmol), methyl-4-iodophenylacetate (0.063 g, 0.23 mmol), triethyl amine (8 mL), copper(I)iodide (0.018 g, 0.093 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.065 g, 0.093 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 5–20% ethyl acetate in hexane as the eluent, the title compound was obtained as a yellow solid (0.09 g, 90%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07226951B2
Source datasetuspto-grants-2007_06
ORD IDord-6090338dff12477ba395b37c3a4c8916
Source noteuspto-grants-2007_06