Sodium Sulfate → Ethyl 2-(methoxyimino)-4-oxopentanoate

HRID 2261727Notes

Reaction equation

HRID 2261727 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C:5](=O)[CH2:6][C:7](=[O:9])[CH3:8])[CH3:2].Cl.[CH3:13][O:14][NH2:15].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:11])[C:5](=[N:15][O:14][CH3:13])[CH2:6][C:7](=[O:9])[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 69208Ethyl 2,4-dioxovalerateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 589173Ethyl 2-(methoxyimino)-4-oxopentanoateYield 32.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-dioxo-pentanoic acid ethyl ester (5.4 mL, 50 mmol), methoxyamine hydrochloride (4.4 g, 52.5 mmol), molecular sieves (3 Å, 35 g) and sodium sulfate (15 g) in ethanol (50 mL) is stirred at ambient temperature for 5 hours. The reaction mixture is filtered and washed with ethanol. The combined filtrate is concentrated under reduced pressure and is partitioned between ethyl ether and saturated sodium bicarbonate. The organic layer is dried (MgSO4), filtered, and concentrated. The residue is purified by column chromatography (0 to 15% EtOAc in hexanes) to give the title compound as a colorless oil (3 g, 32%). 1H NMR (400 MHz, CDCl3) δ 4.33 (q, 2H), 4.06 (s, 3H), 3.70 (s, 3H), 2.20 (s, 3H), 1.34 (t, 3H).

Workup

  1. filtrationThe reaction mixture is filtered
  2. washwashed with ethanol
  3. concentrationThe combined filtrate is concentrated under reduced pressure
  4. customis partitioned between ethyl ether and saturated sodium bicarbonate
  5. dry with materialThe organic layer is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography (0 to 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b0107a86403a4c3e84e1a559973ba69c
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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