Reacción #476218

Ecuación de reacción

5-Chloro-2-pentanone

methyl (4-piperidin-4-ylidene-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-yl)acetate

potassium carbonate

potassium iodide

→

captioned compound

Rendimiento 78.0%

Methyl {4-[1-(4-oxopentyl)piperidin-4-ylidene]-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-yl}acetate

Rendimiento 78.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONThe solvents were distilled off under a reduced pressure, water
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   Extracciónthe product was extracted with ethyl acetate
4. 4
   SecadoThe organic layer was dried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONthe solvents were then distilled off under a reduced pressure
6. 6
   OtroThe residue was purified by column chromatography (chloroform:methanol=19:1)

Procedimiento

5-Chloro-2-pentanone (2.4 mL, 20.9 mmol) was added to a DMF (50 mL) solution of methyl (4-piperidin-4-ylidene-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-yl)acetate (2.50 g, 7.0 mmol), anhydrous potassium carbonate (2.15 g, 15.6 mmol), and potassium iodide (1.41 g, 8.5 mmol), and the mixture was stirred overnight at 80° C. The solvents were distilled off under a reduced pressure, water was added to the residue, and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvents were then distilled off under a reduced pressure. The residue was purified by column chromatography (chloroform:methanol=19:1), to give 2.40 g (78%) of the captioned compound in the form of an oily product.

Fuente