Ethyl isobutyrylacetate → HCID 178472908, compound

HRID 1605414Notes

Reaction equation

HRID 1605414 reaction equation
[N:1]([O-:3])=O.[Na+].[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:9])[CH:6]([CH3:8])[CH3:7]>O.C(O)(=O)C>[N:1](=[C:10]([C:5](=[O:9])[CH:6]([CH3:8])[CH3:7])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[OH:3]

Participants

5

Reactant 2

HCID 81583Ethyl isobutyrylacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178472908HCID 178472908, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (43.8 g.) in water (92 ml.) was added dropwise, with stirring, to a solution of ethyl isobutyrylacetate (100.3 g.) in acetic acid (80 ml.) at 0°. After stirring at 0° for 30 minutes then at room temperature for 3 hours, water (100 ml.) was added and the mixture extracted with ether. The extracts were washed with water, saturated sodium bicarbonate solution and water. After drying (CaSO4), the solution was evaporated to give ethyl 2-oximino-4-methyl-3-oxopentanoate (112 g.) as a crude oil.

Workup

  1. waitat room temperature for 3 hours
  2. extractionthe mixture extracted with ether
  3. washThe extracts were washed with water, saturated sodium bicarbonate solution and water
  4. dry with materialAfter drying (CaSO4)
  5. customthe solution was evaporated

Sources & evidence

ORD record
ord-7fdae5b67b44468f81300efa3eeb6335
Source dataset
uspto-grants-1976_04
Patent number
US03950353

Reaction notes

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