Water → 2-(Methyloxy)-4-(2-oxoethyl)benzonitrile

HRID 1519574ノート

反応式

HRID 1519574 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:11][CH:10]2C(OCC)=O)=[CH:5][C:4]=1[O:17][CH3:18])#[N:2].CC[O-].[Na+].O>C(O)C>[CH3:18][O:17][C:4]1[CH:5]=[C:6]([CH2:9][CH:10]=[O:11])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

参加物

5

反応物 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 86694471Ethyl 3-(4-cyano-3-methoxyphenyl)oxirane-2-carboxylate

生成物 1

HCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of ethyl 3-(4-cyano-3-methoxyphenyl)oxirane-2-carboxylate (400 mg, 1.6 mmol) in 5 mL of dry ethanol was cooled to 0° C. Freshly prepared EtONa (2.1 mmol) in 4 mL of ethanol was added and stirred at 0° C. for 10 min. Then dropwise addition of 0.1 g of water, stirred at 0° C. for 2 hours, and the sodium salt of the epoxy compound was filtered. The sodium salt of the epoxy compound was then dissolved in 10 mL of water and added 10 mL of 1 N of HCl and 20 mL of toluene. The mixture was heated to reflux for 2 hours. The organic phase was separated, washed by saturated sodium chloride, dried over Na2SO4 and distilled off solvent to afford crude 2-methoxy-4-(2-oxoethyl)benzonitrile. MS m/z: 176 (M+1)+.

後処理

  1. stirringstirred at 0° C. for 2 hours
  2. filtrationthe sodium salt of the epoxy compound was filtered
  3. dissolutionThe sodium salt of the epoxy compound was then dissolved in 10 mL of water
  4. additionadded 10 mL of 1 N of HCl and 20 mL of toluene
  5. temperatureThe mixture was heated
  6. temperatureto reflux for 2 hours
  7. customThe organic phase was separated
  8. washwashed by saturated sodium chloride
  9. dry with materialdried over Na2SO4
  10. distillationdistilled off solvent

出典と根拠

ORDレコード
ord-dde40bc9d9dd435aa0f7db05a047adc8
出典データセット
uspto-grants-2015_07
特許番号
US09073882B2

反応ノート

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