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

HRID 572150

反応式

HRID 572150 の反応式
[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]

参加物

5

反応物 4

HCID 176Acetic AcidHCID 1140Toluene2 回HCID 114553-MethylacetophenoneHCID 24758Sodium hydride

生成物 1

HCID 2760277Ethyl 3-(3-methylphenyl)-3-oxopropanoate収率 46.9%

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-4136650b07f44c0eb00d4b54223535c1
出典データセット
uspto-grants-2015_05
特許番号
US09029394B2

関連ノート

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