Diethyl Malonate → Ethyl 2-Ethoxycarbonyl-4-(4-octylphenyl)butyrate

HRID 862852노트

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HRID 862852 반응식
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:13]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28]I)=[CH:23][CH:22]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)C>[CH2:11]([O:10][C:2]([CH:3]([CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:26][CH:25]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:9])[CH3:12]

참가 물질

5

반응물 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 105453621-(2-Iodoethyl)-4-octylbenzene

생성물 1

HCID 21849265Ethyl 2-Ethoxycarbonyl-4-(4-octylphenyl)butyrate수율 65.9%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
40 °C

실험 절차

Sodium (2.67 g) was dissolved in absolute ethanol (100 ml) and diethyl malonate (18.6 g) was dropwise added thereto at 27°-30° C. for 3 minutes. The mixture was stirred at 40° C. for 40 minutes and 2-(4-octylphenyl)ethyl iodide (40 g) was dropwise added to the reaction mixture at 44°-45° C. over 10 minutes. The mixture was refluxed at 50° C. for 1 hour and stirred under heating for 1.5 hours. The reaction mixture was cooled and the solvent was distilled away under reduced pressure. Water was added thereto and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue obtained was subjected to silica gel column chromatography to give the subject compound (28.8 g).

후처리

  1. temperatureThe mixture was refluxed at 50° C. for 1 hour
  2. stirringstirred
  3. temperatureunder heating for 1.5 hours
  4. temperatureThe reaction mixture was cooled
  5. distillationthe solvent was distilled away under reduced pressure
  6. additionWater was added
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate
  10. distillationThe solvent was distilled away under reduced pressure
  11. customthe residue obtained

출처 및 근거

ORD 기록
ord-2489e87f634d4ae2b077fa42029f6f01
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719176

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