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

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

反応物 4

HCID 176Acetic Acid

HCID 1140Toluene2 回

HCID 114553-Methylacetophenone

HCID 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%)