Ozone → Methyl 3-methyl-4-oxobutanoate

Temperature

-78 °C

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 hour, 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.

1. temperatureto warm to room temperature and most of the solvent
2. customis removed in vacuo
3. filtrationThe residue is filtered
4. additionthe filtrate is treated with ether (500 ml)
5. washThe organic phase is washed with water (3×200 ml)
6. dry with materialdried (Na2SO4)
7. customthe solvent is removed in vacuo

ORD record

ord-c3edcff58f2844c888dd8adca8b7bcee

Source dataset

uspto-grants-1980_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04237054