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

HRID 523518Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 160 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-1c355170ec3b482dbf7e99b611e32089
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09339486B2

Reaction notes

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