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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1063452Generated: October 31, 2026

Water → HCID 69338924, compound

https://huagongshe.com/reaction/1063452

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantTriethylamineHCID 8471—
Reactant5-Phenyl-1-pentyneHCID 74573—
ReactantHCID 69338013HCID 69338013—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
ProductHCID 69338924HCID 6933892475%

Reaction Conditions

Temperature80 °C

Reaction Steps

(2R)-Acetylamino-2-methyl-4-(5-bromothiophen-2-yl)butyl acetate (1.60 g, 4.59 mmol) obtained in Example 47 (c) was dissolved in dimethylformamide (16 ml), and 5-phenylpent-1-yne (1.99 g, 13.8 mmol), triethylamine (6.40 ml, 45.9 mmol), copper(I) iodide (175 mg, 0.92 mmol), and dichlorobis(triphenylphosphine)palladium (322 mg, 0.46 mmol) were added thereto followed by stirring for 2 hours at 80° C. under a nitrogen atmosphere. The reaction solution was poured into water, extracted with ethyl acetate, and after the ethyl acetate layer was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=2:1-2:3) to give the title compound (1.41 g, 75% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06964976B2
Source datasetuspto-grants-2005_11
ORD IDord-cb9f688317ed4e9ba8fa80b818ea296f
Source noteuspto-grants-2005_11