Ethyl Acetoacetate → HCID 178472877, compound

HRID 2361570Notes

Reaction equation

HRID 2361570 reaction equation
[N:1]([O-:3])=O.[Na+].[CH2:5]([O:7][C:8](=[O:13])[CH2:9][C:10]([CH3:12])=[O:11])[CH3:6]>O.C(O)(=O)C>[CH2:5]([O:7][C:8](=[O:13])[C:9](=[N:1][OH:3])[C:10](=[O:11])[CH3:12])[CH3:6]

Participants

5

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178472877HCID 178472877, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (36.9 g, 0.534 mol) in 70 mL of water was added dropwise to a stirred solution of ethylacetoacetate (70 g, 0.538 mol) in 1401 mL of glacial acetic acid at 0° C. After the addition was complete, the light yellow reaction mixture was allowed to warm to room temperature. After 30 minutes, all the starting material had been consumed, the reaction was quenched with 350 mL of water and extracted with ethyl acetate (2×125 mL). The organic extracts were combined and washed with water (2×125 mL) and saturated sodium hydrogen carbonate aqueous solution (2×105 mL). The organic layer was dried with sodium sulfate and concentrated in vacuo to give 84.2 g (98%) of ethyl-2-Hydroxyimino-3-oxobutanoate 1b as a pale yellow oil. 1H NMR (CDCl3) δ 10.3 (s, 1H), 4.2 (q, 2H), 2.3 (s, 3H), 1.3 (t, 3H) ppm.

Workup

  1. additionAfter the addition
  2. customall the starting material had been consumed
  3. customthe reaction was quenched with 350 mL of water
  4. extractionextracted with ethyl acetate (2×125 mL)
  5. washwashed with water (2×125 mL) and saturated sodium hydrogen carbonate aqueous solution (2×105 mL)
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d357de17eb2f466d8e1a9b863fed2f06
Source dataset
uspto-grants-2014_04
Patent number
US08691758B2

Reaction notes

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