Reaktion #328546

Reaktionsgleichung

MeONa

MeOH

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

hydrochloric acid

methyl (4-acetyl-2-methylphenyl)acrylate

→

titled compound

Ausbeute 48.0%

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

Ausbeute 48.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling, to which
2. 2
   workup.STIRRINGThe mixture was stirred for 4 hours under ice-
3. 3
   Filtrationfiltered
4. 4
   WaschenThe filtrate was washed with water
5. 5
   Trocknenthe organic layer was dried over anhydrous sodium sulfate
6. 6
   SonstigeThe solvent was removed under reduced pressure
7. 7
   Sonstigethe residue was recrystallized from ethyl acetate/hexane

Vorschrift

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%).

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