Diethyl Oxalate → Ethyl 2,4-dioxo-4-(2,4,6-trimethylphenyl)butanoate

HRID 1152

반응식

HRID 1152 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10](=[O:12])[CH3:11].[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].[H-].[Na+]>C1(C)C=CC=CC=1>[O:19]=[C:13]([CH2:11][C:10](=[O:12])[C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

참가 물질

5

반응물 3

HCID 7268Diethyl OxalateHCID 15461Ethanone, 1-(2,4,6-trimethylphenyl)-HCID 24758Sodium hydride

생성물 1

HCID 14945000Ethyl 2,4-dioxo-4-(2,4,6-trimethylphenyl)butanoate수율 66.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 2', 4', 6'-trimethylacetophenone (15 g, 92.6 mmol) and diethyl oxalate (20 g, 139 mmol) in 500 mL of anhydrous toluene was cautiously added 7.4 g of NaH (60% dispersion in mineral oil). The reaction mixture was slowly heated to reflux under N2. It was refluxed for about 20 minutes, then cooled, poured into ice-cold aqueous HCl solution, and extracted with ether. The extracts were washed with brine, dried over Na2SO4, filtered through a short silica gel pad and concentrated to give 16.2 g of a red oil which was used in the next reaction without further purification.

후처리

  1. temperatureThe reaction mixture was slowly heated
  2. temperatureto reflux under N2
  3. temperatureIt was refluxed for about 20 minutes
  4. temperaturecooled
  5. additionpoured into ice-cold aqueous HCl solution
  6. extractionextracted with ether
  7. washThe extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered through a short silica gel pad
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-54fc6a8a376c4fd9a41d798a9116e90e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723608

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