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

HRID 233438노트

반응식

HRID 233438 반응식
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]

참가 물질

3

반응물 2

HCID 10541Trimethyl PhosphateHCID 154634-Phenylbenzyl chloride

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5b23c166a0b34b7899d06d38da820797
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593980

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