Reacción #7915

Ecuación de reacción

5-methoxy-2-methyl-1-indanone

1,8-diazabicyclo[5.4.0]undec-7-ene

methyl vinyl ketone

→

5-methoxy-2-methyl-2-(3-oxo-butyl)-1-indanone

Disolventes

tetrahydrofuran

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 0.2N HCl (25 mL) and brine (10 mL)
2. 2
   Secadodried over MgSO4
3. 3
   Filtraciónfiltered
4. 4
   Otroevaporated under vacuum to a yellow oil (800 mg)
5. 5
   workup.DISSOLUTIONThe oil was dissolved in CH2Cl2 (10 mL)
6. 6
   workup.ADDITIONthe solution added to a small column of EM silica gel 60 (8 mL)
7. 7
   LavadoThe column was eluted with CH2Cl2 (30 ml)
8. 8
   Otrothe eluant evaporated under vacuum

Procedimiento

A solution of 5-methoxy-2-methyl-1-indanone (0.5 g, 2.84 mmol) in anhydrous tetrahydrofuran (3 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (0.085 mL, 0.57 mmol) and methyl vinyl ketone (0.473 mL, 5.68 mmol). The resulting solution was placed under a nitrogen atmosphere and stirred at room temperature overnight. The mixture was diluted with EtOAc (25 mL), washed with 0.2N HCl (25 mL) and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to a yellow oil (800 mg). The oil was dissolved in CH2Cl2 (10 mL) and the solution added to a small column of EM silica gel 60 (8 mL). The column was eluted with CH2Cl2 (30 ml) and the eluant evaporated under vacuum to afford 5-methoxy-2-methyl-2-(3-oxo-butyl)-1-indanone (467 mg) as an oil.

Fuente