Trimethyl Phosphate → ([1,1'-Biphenyl]-4-ylmethyl)phosphonic acid dimethyl ester
反応式
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:15][O:16][P:17](OC)([O:19][CH3:20])=[O:18]>>[CH3:15][O:16][P:17]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)(=[O:18])[O:19][CH3:20]参加物
3
実験手順
A solution of 4-(chloromethyl)biphenyl (4.12 g, 0.020M) in trimethylphosphate (10 mL, 10.5 g, 0.085M) is heated at reflux temperature for 60 hours. The excess trimethylphosphite is removed under reduced pressure and the solid residue is chromatographed (400 g of 40-63 μm silica gel, 50 mL fractions). The sample is applied to the column in a minimum amount of EtOAc and the column is eluted with 50% EtOAc-hexane (1.2 L), 75% EtOAc-hexane (2 L), and with EtOAc. Fractions 88-136 contained the dimethyl ester (4.98 g, 0.0180M, 90%) which is crystallized from ether-pentane to give 4.09 g of title compound as white crystals, mp 70°-71° C.(fused), 76.5°-77.5° C.
後処理
- temperatureat reflux temperature for 60 hours