Reaktion #55630

Reaktionsgleichung

ozone

methyl 3-methyl-4-nitrobutanoate

sodium methoxide

→

methyl 3-methyl-4-oxo-butanoate

Lösungsmittel

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature and most of the solvent
2. 2
   Sonstigeis removed in vacuo
3. 3
   FiltrationThe residue is filtered
4. 4
   workup.ADDITIONthe filtrate is treated with ether (500 ml)
5. 5
   WaschenThe organic phase is washed with water (3×200 ml)
6. 6
   Trocknendried (Na2SO4)
7. 7
   Sonstigethe solvent is removed in vacuo

Vorschrift

A solution of methyl 3-methyl-4-nitrobutanoate (96 g, 0.596 m) in methanol (30 ml) is added dropwise to a solution of sodium methoxide (34.5 g, 0.638 m) in methanol (1 l) at room temperature under nitrogen. The resulting mixture is stirred for 1 hr., cooled to -78° C. and treated with one equivalent of ozone. The reaction mixture is then allowed to warm to room temperature and most of the solvent is removed in vacuo. The residue is filtered and the filtrate is treated with ether (500 ml). The organic phase is washed with water (3×200 ml), dried (Na2SO4) and the solvent is removed in vacuo to give the crude product, methyl 3-methyl-4-oxo-butanoate (86.3 g). This material is used directly in the next step.

Quelle