Tetrahydrofuran → 1,3-Bis(diethylphosphonooxy)-4-ethylbenzene

HRID 449790ノート

反応式

HRID 449790 の反応式
[O:1]1[CH2:5][CH2:4]CC1.[CH2:6]([C:8]1[CH:14]=[CH:13][C:11]([OH:12])=[CH:10][C:9]=1[OH:15])[CH3:7].[H-].[Na+].[P:18](Cl)([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19]>O>[CH2:21]([O:20][P:18]([O:12][C:11]1[CH:13]=[CH:14][C:8]([CH2:6][CH3:7])=[C:9]([O:15][P:18]([O:1][CH2:5][CH3:4])([O:20][CH2:21][CH3:22])=[O:19])[CH:10]=1)([O:23][CH2:24][CH3:25])=[O:19])[CH3:22]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 13139Diethyl chlorophosphateHCID 179274-EthylresorcinolHCID 24758Sodium hydride

生成物 1

HCID 545972611,3-Bis(diethylphosphonooxy)-4-ethylbenzene収率 100%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a tetrahydrofuran solution (10 ml) of 4-ethylresorcinol (691 mg), sodium hydride (60% dispersion in liquid paraffin) (440 mg) was added and stirred at 0° C. for 30 minutes. Then, diethyl chlorophosphate (1.73 ml) was added dropwise. After stirring at room temperature for 3 hours, water (10 ml) was added to the reaction mixture, and the extraction was carried out with ethyl acetate (30 ml). Then, the extract was washed with saturated brine (10 ml), dried with anhydrous sodium sulfate and then concentrated. The residue (2.43 g) was subjected to silica gel chromatography (silica gel 40 g, chloroform to chloroform:methanol=10:1), to give the title compound (2.05 g, yield: 100%) as a pale yellow oil.

後処理

  1. stirringAfter stirring at room temperature for 3 hours
  2. extractionthe extraction
  3. washThen, the extract was washed with saturated brine (10 ml)
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-42cc9b0905be40cca21db77815f602f9
出典データセット
uspto-grants-2013_07
特許番号
US08486919B2

反応ノート

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