Potassium Carbonate → 3-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 2092974Notes

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+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>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][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([CH3:14])[CH2:12][O:11][C:6]=2[CH:5]=1)=[O:16]

Participants

Conditions

Temperature: 115 °C

Procedure

To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (455 mg, 1.37 mmol) obtained in Example 4(A), in DMF (15 mL) were added Potassium carbonate (379 mg, 2.74 mmol), Tetrabutylammonium chloride (380 mg, 1.37 mmol), Palladium acetate (25.6 mg, 0.136 mmol) in DMF (5 mL) and Phenylboronic acid (200 mg, 1.64 mmol). The resulting mixture was stirred for 3 h at 115° C., cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded 368 mg (95%) of the title compound as a slightly brown oil which crystallize. Mp:52° C.

Workup

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

Sources & evidence

ORD record: ord-71211b68acd349369b3a909a420c2d86
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440832B2

Reaction notes

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