Tetrahydrofuran → Dimethyl (3,3-dimethyl-2-oxo-4-phenylbutyl)phosphonate

HRID 437106

반응식

HRID 437106 반응식
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].O1CCCC1.C([Li])CCC.[CH3:18][C:19]([CH3:30])([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:20](Cl)=[O:21]>CCCCCC.C(O)(=O)C>[CH3:18][C:19]([CH3:30])([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:20](=[O:21])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

참가 물질

7

반응물 4

HCID 8028Tetrahydrofuran2회HCID 12958Dimethyl methylphosphonateHCID 133072292,2-Dimethyl-3-phenylpropanoyl chlorideHCID 178418339Butyllithium

생성물 1

HCID 14302191Dimethyl (3,3-dimethyl-2-oxo-4-phenylbutyl)phosphonate

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8058Hexane용매

실험 절차

To a solution of 63 g. of dimethyl methylphosphonate in 600 ml. of tetrahydrofuran under nitrogen atmosphere at -75° C. is added with stirring 312 ml. of 1.6 M n-butyllithium in hexane. The condition is regulated so as to maintain a reaction temperature below -55° C. Ten minutes after the addition, 48.2 g. of the reaction product of step B above (2,2-dimethyl-3-phenylpropionyl chloride) in 15 ml. of tetrahydrofuran is added dropswise. The dropwise addition is regulated so as to maintain a reaction temperature below -60° C. The mixture is stirred at -75° C. for 2 hr. and at ambient temperature overnight. Acetic acid (20 ml.) is added and the tetrahydrofuran is removed by distillation. The residue is shaken with diethyl ether-methylene chloride (3:1, by volume) and dilute sodium bicarbonate solution. The organic layer is washed with saturated saline and then dried and concentrated. The residue is recrystallized in diethyl ether to give 54 g. of the title compound of this preparation. Melting point 49°-51° C.

후처리

  1. temperatureto maintain a reaction temperature below -55° C
  2. additionTen minutes after the addition, 48.2 g
  3. additionThe dropwise addition
  4. temperatureto maintain a reaction temperature below -60° C
  5. stirringThe mixture is stirred at -75° C. for 2 hr
  6. customat ambient temperature
  7. customovernight
  8. customthe tetrahydrofuran is removed by distillation
  9. stirringThe residue is shaken with diethyl ether-methylene chloride (3:1, by volume) and dilute sodium bicarbonate solution
  10. washThe organic layer is washed with saturated saline
  11. customdried
  12. concentrationconcentrated
  13. customThe residue is recrystallized in diethyl ether
  14. customto give 54 g

출처 및 근거

ORD 기록
ord-7298d8885ce0402f8c54de50c8a687e8
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04029693

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