Methyl vinyl ketone → 5-Methoxy-2-methyl-2-(3-oxo-butyl)-1-indanone

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.

1. washwashed with 0.2N HCl (25 mL) and brine (10 mL)
2. dry with materialdried over MgSO4
3. filtrationfiltered
4. customevaporated under vacuum to a yellow oil (800 mg)
5. dissolutionThe oil was dissolved in CH2Cl2 (10 mL)
6. additionthe solution added to a small column of EM silica gel 60 (8 mL)
7. washThe column was eluted with CH2Cl2 (30 ml)
8. customthe eluant evaporated under vacuum

ORD-Eintrag

ord-b2f702acf9204650b931ca10badf77fa

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07087599B2