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

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Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7](I)=[C:6]([O:11][CH2:12][C:13]([CH3:15])=[CH2:14])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH:23](B(O)O)=[CH:24][CH2:25][CH2:26][CH3:27]>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[C:13]([CH2:15]/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH3:27])([CH3:14])[CH2:12][O:11][C:6]=2[CH:5]=1)=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

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.

Aufarbeitung

temperaturecooled to room temperature
filtrationfiltered over silica
washwashed with water
dry with materialdried over MgSO4
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-81fb000a019a4244b00f562b18a2be2d
Quelldatensatz: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08440832B2

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