반응 #328546

반응 방정식

MeONa

MeOH

3-methyl-6-(trifluoromethyl)benzothiophen-2-carboxaldehyde

hydrochloric acid

methyl (4-acetyl-2-methylphenyl)acrylate

→

titled compound

수율 48.0%

Methyl 3-[4-[3-[3-methyl-6-(trifluoromethyl)benzothiophen-2-yl]propenoyl]-2-methylphenyl]acrylate

수율 48.0%

용매

THF

THF

반응 조건

후처리

1. 1
   온도cooling, to which
2. 2
   workup.STIRRINGThe mixture was stirred for 4 hours under ice-
3. 3
   여과filtered
4. 4
   세척The filtrate was washed with water
5. 5
   건조the organic layer was dried over anhydrous sodium sulfate
6. 6
   기타The solvent was removed under reduced pressure
7. 7
   기타the residue was recrystallized from ethyl acetate/hexane

실험 절차

To an ice-cold suspension of methyl (4-acetyl-2-methylphenyl)acrylate [WO 2007119887] (89 mg, 0.41 mmol) and powdered Molecular sieves 3A (250 mg) in THF (2 mL) was added 0.5M MeONa in MeOH (1.0 mL, 0.49 mmol) under N2 atmosphere. The mixture was stirred for 10 minutes under ice-cooling, to which was added slowly a solution of 3-methyl-6-(trifluoromethyl)benzothiophen-2-carboxaldehyde (100 mg, 0.410 mmol) in THF (1.7 mL). The mixture was stirred for 4 hours under ice-cooling, neutralized with 1N hydrochloric acid, and filtered. The filtrate was washed with water, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the titled compound as a yellow crystal (87 mg, 48%).

출처