Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:18])[CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]1[O:11][CH2:10][CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([C:12]([O:11][CH3:10])=[O:13])=[CH:3][CH:4]=1)[CH3:18]To the solution of 2-(3-(4-bromophenyl)butoxy)-tetrahydro-2H-pyran (1.05 mg, 3.37 mmol) in methanol (30 mL) was added 1,3-bis(diphenylphosphino) propane (278 mg, 0.67 mmol), palladium acetate (151 mg, 0.67 mmol), and triethylamine (1.7 g, 16.9 mmol), the mixture was stirred at 90° C. for 12 hours under an atmosphere of carbon monoxide in sealed tube. Then the mixture was concentrated and purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1) to give methyl 4-(4-(tetrahydro-2H-pyran-2-yloxy)butan-2-yl)benzoate (501.8 mg, 51%).
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