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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 546834Generated: October 25, 2026

Ethyl Acetate → HCID 57443484, compound

https://huagongshe.com/reaction/546834

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium CarbonateHCID 10340—
ReactantMethyl 5-bromofuran-2-carboxylateHCID 599633—
Reactant4-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenolHCID 57709170—
SolventTolueneHCID 1140—
ProductHCID 57443484HCID 5744348473.9%

Reaction Conditions

Temperature85 °C

Reaction Steps

5-Bromo-furan-2-carboxylic acid methyl ester (J. Org. Chem., 1988, 53(9), 2099.; 156 mg, 0.761 mmol), tetrakistriphenylphosphine palladium (15 mg, 0.013 mmol) and a 2 M sodium carbonate aqueous solution (0.3 mL, 0.6 mmol) were added to a solution of 4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol (Example 15-(2); 100 mg, 0.254 mmol) in toluene (0.5 mL) at room temperature, and the mixture was stirred at 85° C. for 17 hours. Ethyl acetate was added to the reaction solution. The organic layer was filtered through celite, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1) to give the title compound (73.6 mg, 73.9%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07935688B2
Source datasetuspto-grants-2011_05
ORD IDord-17745f86694140fba6cd1dd396d317c0
Source noteuspto-grants-2011_05