Trimethyl Phosphate → ([1,1'-Biphenyl]-4-ylmethyl)phosphonic acid dimethyl ester

HRID 233438

反応式

HRID 233438 の反応式
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

反応物 2

HCID 10541Trimethyl PhosphateHCID 154634-Phenylbenzyl chloride

生成物 1

HCID 15359635([1,1'-Biphenyl]-4-ylmethyl)phosphonic acid dimethyl ester収率 72.8%

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

  1. temperatureat reflux temperature for 60 hours
  2. customThe excess trimethylphosphite is removed under reduced pressure
  3. customthe solid residue is chromatographed (400 g of 40-63 μm silica gel, 50 mL fractions)
  4. washthe column is eluted with 50% EtOAc-hexane (1.2 L), 75% EtOAc-hexane (2 L)
  5. customis crystallized from ether-pentane

出典と根拠

ORDレコード
ord-5b23c166a0b34b7899d06d38da820797
出典データセット
uspto-grants-1997_01
特許番号
US05593980

関連ノート

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