Water → Methyl-chloromethylene-cyanoacetate

HRID 2230921ノート

反応式

HRID 2230921 の反応式
[Na].[CH3:2][O:3][C:4](=[O:10])[C:5](=[CH:8]O)[C:6]#[N:7].P(Cl)(Cl)(Cl)(Cl)[Cl:12].O>ClCCl>[CH3:2][O:3][C:4](=[O:10])[C:5](=[CH:8][Cl:12])[C:6]#[N:7]

参加物

6

反応物 4

HCID 962WaterHCID 24819Phosphorus pentachlorideHCID 3021154Methyl 2-cyano-3-hydroxy-2-propenoateHCID 5360545Sodium

生成物 1

HCID 71444203Methyl-chloromethylene-cyanoacetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

To a suspension of the sodium salt of methylhydroxymethylene-cyanoacetate (19.0 g, 127 mmol) in 200 mL of dichloromethane was added phosphorous pentachloride (26.5 g, 127 mmol) in one portion. The reaction mixture was allowed to exotherm to reflux temperature and then maintained at reflux with stirring for 4 hours. The resulting light yellow suspension was allowed to cool to 23° C. and then poured into 400 mL of cold water. The mixture stirred for 15 minutes and the phases were separated. The aqueous layer was extracted with 100 mL of dichloromethane and the combined organic layers were washed twice with water, dried over magnesium sulfate, and concentrated to 16.8 g of the title compound which was of sufficient purity for use in Example 1. 1H NMR (300 MHz, CDCl3) δ 3.88 (s, 3H), 7.58 (s, 0.35H), 8.04 (s, 0.65H).

後処理

  1. temperatureto reflux temperature
  2. temperaturemaintained
  3. temperatureat reflux
  4. stirringThe mixture stirred for 15 minutes
  5. customthe phases were separated
  6. extractionThe aqueous layer was extracted with 100 mL of dichloromethane
  7. washthe combined organic layers were washed twice with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated to 16.8 g of the title compound which

出典と根拠

ORDレコード
ord-0afdbc3862094965b155ac02da0381a9
出典データセット
uspto-grants-2002_07
特許番号
US06426417B1

反応ノート

読み込み中…