Phenethyl bromide → Diethyl 2-phenylethyl phosphonate

HRID 485595ノート

反応式

HRID 485595 の反応式
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[H-].[Na+].[CH2:11](Br)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH2:3]([O:2][P:1]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:4]

参加物

5

反応物 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 3780918Diethylphosphite

生成物 1

HCID 3448525Diethyl 2-phenylethyl phosphonate収率 51.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-15 °C

実験手順

Diethyl phosphite (27.64 g, 200 m mole) was dissolved in DMF (200 ml), and to the solution at nitrogen atmosphere while stirring and -15° C., sodium hydride (60% in oil, 9.6 g, 220 m mole) was added. The mixture was stirred for 1 hour at not more than 0° C. To the solution phenethyl bromide (37.0 g, 200 m mole) was dropwise added and further the mixture was stirred overnight at room temperature. DMF was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with water, and dried with anhydrous sodium sulfate. The solvent was evaporated and the thus obtained oily product was distilled under reduced pressure to obtain diethylphenethylphosphonate (25.0 g, yield: 51.6%) of boiling point 136.5~137.5° C./3 mmHg.

後処理

  1. stirringThe mixture was stirred for 1 hour at not more than 0° C
  2. stirringfurther the mixture was stirred overnight at room temperature
  3. distillationDMF was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. distillationthe thus obtained oily product was distilled under reduced pressure

出典と根拠

ORDレコード
ord-7c5f995c6a5f42f18e9fa1aeb49db21d
出典データセット
uspto-grants-1985_08
特許番号
US04536395

反応ノート

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