Acetic Acid → Ethyl 3-(3-methylphenyl)-3-oxopropanoate

HRID 572150

반응식

HRID 572150 반응식
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:12])=[O:11])[CH:7]=[CH:6][CH:5]=1.C[C:14]([OH:16])=[O:15].[C:17]1(C)C=CC=C[CH:18]=1>>[CH3:3][C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][CH:5]=1)[C:10]([CH2:12][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11]

참가 물질

5

반응물 4

HCID 176Acetic AcidHCID 1140Toluene2회HCID 114553-MethylacetophenoneHCID 24758Sodium hydride

생성물 1

HCID 2760277Ethyl 3-(3-methylphenyl)-3-oxopropanoate수율 46.9%

실험 절차

To a vigorously stirred suspension of NaH (564 mg, 48.5 mmol) and CO(OEt)2 (5.73 g, 48.5 mmol) in anhydrous toluene (50 ml) was added dropwise a solution of 3-methylacetophenone (4.33 g, 32.3 mmole) in toluene under reflux. The mixture was allowed to reflux and was stirred for 30 min after the addition was complete. When cooled to room temperature, the mixture was acidified with glacial AcOH. After ice-cold water was added, the mixture was extracted with toluene. The organic layer was dried over MgSO4, and evaporated. The residue was further chromatographed over silica gel by elution with CH2Cl2-n-haxane (3:2) to afford I-10-b as light-yellow liquid (3.13 g, 46.9%)

후처리

  1. temperatureunder reflux
  2. temperatureto reflux
  3. additionafter the addition
  4. additionAfter ice-cold water was added
  5. extractionthe mixture was extracted with toluene
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated
  8. customThe residue was further chromatographed over silica gel by elution with CH2Cl2-n-haxane (3:2)

출처 및 근거

ORD 기록
ord-4136650b07f44c0eb00d4b54223535c1
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029394B2

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