Ethyl isobutyrylacetate → HCID 178472908, compound

HRID 2398337Notes

Reaction equation

HRID 2398337 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-dc185c662da64f12972afb15191d5d9c
Source dataset
uspto-grants-1977_05
Patent number
US04024271

Reaction notes

Loading…