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

HRID 1519574노트

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HRID 1519574 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
0 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-dde40bc9d9dd435aa0f7db05a047adc8
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073882B2

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