Water → Dimethyl 3-(2-methoxy-2-oxoethyl)pentanedioate

HRID 532078Notes

Reaction equation

HRID 532078 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5](=[CH:11][C:12]([O:14][CH3:15])=[O:13])[CH2:6][C:7]([O:9][CH3:10])=[O:8].O>CO.[Pd]>[CH3:10][O:9][C:7](=[O:8])[CH2:6][CH:5]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:4][C:3]([O:2][CH3:1])=[O:16]

Participants

5

Reactant 2

HCID 962WaterHCID 120538503(Methoxycarbonylmethylene)glutaric acid dimethylester

Product 1

HCID 19038603Dimethyl 3-(2-methoxy-2-oxoethyl)pentanedioate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(methoxycarbonylmethylene)glutaric acid dimethylester (89 g, 267 mmol) in methanol (200 ml) was shaken with (10% palladium on charcoal: 50% water) (9 g) under an atmosphere of hydrogen gas (3.5 bar) for (30 h). The solution was filtered through kieselguhr and concentrated in vacuo to give 3-(methoxycarbonylmethyl)glutaric acid dimethylester as an oil, yield (84.9 g, 94%).

Workup

  1. filtrationThe solution was filtered through kieselguhr
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1def1c3b86754cae9b14e916e672c4da
Source dataset
uspto-grants-2014_10
Patent number
US08852550B2

Reaction notes

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