Water → 3-Cyano-1-diethoxyphosphinylpropanesulfonic acid lithium salt

HRID 2695

反応式

HRID 2695 の反応式
[Li+].[CH2:2]([O:4][P:5]([CH2:10][S:11]([O-:14])(=[O:13])=[O:12])([O:7][CH2:8][CH3:9])=[O:6])[CH3:3].C([Li:19])CCC.[C:20](#[N:23])[CH:21]=[CH2:22].O>O1CCCC1.C(O)(=O)C>[Li+:19].[C:20]([CH2:21][CH2:22][CH:10]([P:5]([O:7][CH2:8][CH3:9])([O:4][CH2:2][CH3:3])=[O:6])[S:11]([O-:14])(=[O:13])=[O:12])#[N:23]

参加物

7

反応物 4

HCID 962WaterHCID 7855AcrylonitrileHCID 23683927Lithium (diethoxyphosphoryl)methanesulfonateHCID 178418339Butyllithium

生成物 1

HCID 883520073-Cyano-1-diethoxyphosphinylpropanesulfonic acid lithium salt

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A suspension of 2.38 g (0.01 mole) of diethoxyphosphinylmethanesulfonate lithium salt (Carretero, et al.; Tetrahedron, 43, 5125 (1987)) in 50 ml of anhydrous tetrahydrofuran is stirred in a -40° bath under a dry nitrogen atmosphere. To this is added n-butyl lithium (4.4 ml of 2.5M solution in hexanes; 0.011 mole) via syringe over 5 minutes. The reaction mixture is allowed to warm to -15° and is stirred at this temperature for about one hour. To it is then added rapidly a solution of 0.53 g (0.01 mole) of acrylonitrile in 3 ml of anhydrous THF. The reaction mixture is stirred for 1 hour at -15° , and is then allowed to warm to room temperature over several hours as the bath warms up. It is stirred at ambient temperature for several hours, and then is quenched by addition of 50 ml of water containing 0.6 g (0.01 mole) of acetic acid. The reaction mixture is concentrated under vacuum on a rotary evaporator to get rid of the THF, and the aqueous layer is extracted with ether to remove some impurities. The water layer is evaporated to dryness under vacuum, and the resulting residue is purified by flash chromatography on silica gel using chloroform/methanol as eluant, to afford 3-cyano-1-diethoxyphosphinylpropanesulfonic acid lithium salt.

後処理

  1. temperatureto warm to -15°
  2. stirringis stirred at this temperature for about one hour
  3. stirringThe reaction mixture is stirred for 1 hour at -15°
  4. stirringIt is stirred at ambient temperature for several hours
  5. concentrationThe reaction mixture is concentrated under vacuum on a rotary evaporator
  6. customto get rid of the THF
  7. extractionthe aqueous layer is extracted with ether
  8. customto remove some impurities
  9. customThe water layer is evaporated to dryness under vacuum
  10. customthe resulting residue is purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-a3dd7bd8f8c04710b88cd5e838b3da7e
出典データセット
uspto-grants-1998_03
特許番号
US05731299

関連ノート

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