p-Toluenesulfonic acid → (3E)-4,4-dimethoxy-3-methoxyiminopentan-2-one

HRID 2306147

Reaction equation

HRID 2306147 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8](=[O:10])[CH3:9])[C:5](=[O:7])[CH3:6].[CH:11](OC)(OC)[O:12]C.[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2]/[N:3]=[C:4](/[C:8]([O:12][CH3:11])([O:10][CH3:18])[CH3:9])\[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 536122Diacetyl(methoxyimino)methane

Product 1

HCID 11263949(3E)-4,4-dimethoxy-3-methoxyiminopentan-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

4.3 g (0.03 mol) of pentane-2,3,4-trione 3-(O-methyloxime) and 6.2 g (0.06 mol) of trimethyl orthoformate were dissolved in 15 ml of methanol and admixed with a spatula tip of p-toluenesulfonic acid. The mixture was subsequently stirred at 50° C. for 5 h, after which the solvent was distilled off. This gave 5.5 g of an oil (98% yield) (phys. data see Tab. 1).

Workup

  1. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-38e7166334d248c4a58ba74da6ee54ed
Source dataset
uspto-grants-2002_08
Patent number
US06441236B1

Linked notes

Loading…