Reaktion #1447130

Reaktionsgleichung

sodium hydride

2.6-diaza-bicyclo[5.2.0]non-1(7)-ene-8,9-dione

2.6-Diaza-bicyclo[5.2.0]non-1(7)-ene-8,9-dione

diethyl 3,3′-[(vinylphosphoryl)bis(oxy)]dibenzoate

Diethyl 3,3′-[(vinylphosphoryl)bis(oxy)]dibenzoate

→

desired title compound

Ausbeute 27.0%

Diethyl 3,3′-[({2-[8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl]ethyl}phosphoryl)bis(oxy)]dibenzoate

Ausbeute 27.0%

Lösungsmittel

N,N-dimethylformamide

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas treated under dry nitrogen
2. 2
   Einengenconcentrated in vacuo
3. 3
   Sonstigethe residue partitioned between 5% aqueous ammonium chloride solution and ethyl acetate (2×60 mL)
4. 4
   WaschenThe organic layers were washed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated to dryness
8. 8
   Sonstigechromatographed on silica gel (60 g)
9. 9
   WaschenElution with 2% methanol in chloroform

Vorschrift

A suspension of 2.6-diaza-bicyclo[5.2.0]non-1(7)-ene-8,9-dione (2) (4 mmol, 608 mg) in N,N-dimethylformamide (60 mL) was treated under dry nitrogen and under stirring with 60% sodium hydride in oil (4.1 mmol, 164 mg). After 30 minutes at ambient temperature the yellow reaction mixture was cooled to 0° C. and a solution of diethyl 3,3′-[(vinylphosphoryl)bis(oxy)]dibenzoate (3) (4 mmol, 1.618 g) in N,N-dimethylformamide (30 mL) was added at once under vigorous stirring. The reaction mixture was then stirred at ambient temperature overnight, concentrated in vacuo and the residue partitioned between 5% aqueous ammonium chloride solution and ethyl acetate (2×60 mL). The organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness. The residue (>1.5 g) was flash chromatographed on silica gel (60 g). Elution with 2% methanol in chloroform afforded 600 mg (27%) of the desired title compound as a white powder; mp 116-7° C. MS (ES+): m/e 557.2 [M+H]+.

Quelle