Ethyl isobutyrylacetate → HCID 178472908, compound

HRID 904365Notes

Reaction equation

HRID 904365 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-09d903afafec42cd881d4b3e6973ef10
Source dataset
uspto-grants-1980_10
Patent number
US04230865

Reaction notes

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