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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1053727Generated: November 3, 2026

Potassium Carbonate → 3-((E)-Hex-2-enyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

https://huagongshe.com/reaction/1053727

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant1-Pentenylboronic acidHCID 2734609—
Reactant4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl esterHCID 25129045—
CatalystTetrabutylammonium ChlorideHCID 70681—
Catalystpalladium(II) acetateHCID 167845—
SolventDimethylformamideHCID 6228—
Product3-((E)-Hex-2-enyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterHCID 68481233—

Reaction Conditions

Temperature160 °C

Reaction Steps

To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (65 mg, 0.2 mmol) in DMF (2 mL) were added Potassium carbonate (54 mg, 0.39 mmol), Tetrabutylammonium chloride (54 mg, 0.2 mmol), Palladium acetate (3.5 mg, 0.02 mmol) in DMF (5 mL) and 1-Penten-1-ylboronic acid, (26 mg, 0.23 mmol). The resulting mixture was stirred under microwave irradiation (160° C., 15 min), cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded title compound as a slightly colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09394267B2
Source datasetuspto-grants-2016_07
ORD IDord-19d1fab33a814dd4869d08afb22a5e8c
Source noteuspto-grants-2016_07