Reaktion #457490

Reaktionsgleichung

Triethyl phosphite

dimethyl acetal

3-Methoxy-5-nitro-benzaldehyde Dimethyl Acetal

boron trifluoride etherate

→

phosphonate

Ausbeute 86.8%

Diethyl 1-methoxy-1-(3-methoxy-5-nitrophenyl)methane Phosphonate

Ausbeute 86.8%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter warming
2. 2
   Sonstigethe reaction to room temperature overnight
3. 3
   Sonstigethe solution was partitioned with 3N HCl
4. 4
   Waschenthe aqueous layer was washed with CH2Cl2 twice
5. 5
   WaschenThe organic layers were washed with dilute NaHCO3
6. 6
   Trocknendried over Na2SO4
7. 7
   Sonstigedecanted
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe crude residue was purified on a silica gel column
10. 10
    Wascheneluting with 0-80% EtOAc/hexanes

Vorschrift

Triethyl phosphite (0.98 ml, 5.7 mmol) was added dropwise to a solution of dimethyl acetal 27 (1.08 g, 4.7 mmol), boron trifluoride etherate (1.2 ml, 9.8 mmol) and CH2Cl2 (10 ml) at 0° C. After warming the reaction to room temperature overnight, the solution was partitioned with 3N HCl and the aqueous layer was washed with CH2Cl2 twice. The organic layers were washed with dilute NaHCO3, dried over Na2SO4, decanted and evaporated. The crude residue was purified on a silica gel column, eluting with 0-80% EtOAc/hexanes, to give 1.36 g (86%) phosphonate 28 as a slightly yellow oil.

Quelle