4-Methyl hydrogen 2-methylenesuccinate → 4-Methoxy-2-methyl-4-oxobutanoic acid

HRID 1615685Notes

Reaction equation

HRID 1615685 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5](=[CH2:9])[C:6]([OH:8])=[O:7]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH:5]([CH3:9])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 817914-Methyl hydrogen 2-methylenesuccinate

Product 1

HCID 45639014-Methoxy-2-methyl-4-oxobutanoic acidYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-methoxy-2-methylene-4-oxobutanoic acid (1.44 g, 10.0 mmol) in MeOH (100 mL) was added 10% Pd on carbon (200 mg). The mixture was stirred under H2 at room temperature for 2 h. The mixture was filtered and the filtrate was concentrated to dryness to give the product as a colorless oil (1.4 g, 96% yield). ESI MS: m/z 147.1 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 3.69 (s, 3H), 2.99-2.94 (m, 1H), 2.77 (d, J=8.0 Hz, 0.5H), 2.73 (d, J=8.4 Hz, 0.5H), 2.46 (d, J=5.6 Hz, 0.5H), 2.42 (d, J=6.4 Hz, 0.5H), 1.27 (d, J=7.6 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-cb9917e41f634b1abfb027d63b1ae461
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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