Trimethyl orthoformate → Methyl (E)-4-Chloro-3-methoxy-2-butenoate

HRID 1165082

反応式

HRID 1165082 の反応式
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5]([CH2:7][Cl:8])=[O:6].[CH3:10]OC(OC)OC>>[CH3:1][O:2][C:3](=[O:9])/[CH:4]=[C:5](/[O:6][CH3:10])\[CH2:7][Cl:8]

参加物

3

反応物 2

HCID 9005Trimethyl orthoformateHCID 36240Methyl 4-chloroacetoacetate

生成物 1

HCID 6364655Methyl (E)-4-Chloro-3-methoxy-2-butenoate収率 75%

反応条件

温度
150 °C

実験手順

31.0 g (0.2 mol) of 4-chloroacetoacetic acid methyl ester is mixed with 106.0 g (1.0 mol) of orthoformic acid trimethyl ester. 30.0 g of Amberlyst-15 ion exchange resin is added under argon with stirring. Under vigorous formation of gas, the reaction temperature rises to 40° C. After 5 hours of stirring, no educt can any longer be detected in thin-layer chromatography. It is filtered from the ion exchange resin and the residue is distilled in a water jet vacuum. The distillate is mixed with 1.0 g of p-toluene sulfonic acid monohydrate and slowly heated to 150° C., and methanol is distilled off. The reaction mass is then distilled in a water jet vacuum. 24.7 g of a colorless liquid with a boiling point bp12 =93° C. is obtained. Further data concerning the compound is:

後処理

  1. addition30.0 g of Amberlyst-15 ion exchange resin is added under argon
  2. customrises to 40° C
  3. stirringAfter 5 hours of stirring
  4. filtrationIt is filtered from the ion exchange resin
  5. distillationthe residue is distilled in a water jet vacuum
  6. additionThe distillate is mixed with 1.0 g of p-toluene sulfonic acid monohydrate
  7. distillationmethanol is distilled off
  8. distillationThe reaction mass is then distilled in a water jet vacuum

出典と根拠

ORDレコード
ord-4eadf34ca9994712bc0d74fdc3ed76c1
出典データセット
uspto-grants-1990_03
特許番号
US04906765

関連ノート

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