Methyl acetoacetate → HCID 178501737, compound

HRID 1428987Notes

Reaction equation

HRID 1428987 reaction equation
[N:1]([O-:3])=O.[Na+].[CH3:5][O:6][C:7](=[O:12])[CH2:8][C:9](=[O:11])[CH3:10]>O>[CH3:5][O:6][C:7](=[O:12])[C:8](=[N:1][OH:3])[C:9](=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178501737HCID 178501737, compoundYield 110.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Part A: NaNO2 (13.8 gram) was dissolved in water (48 ml) at 4° C. The resulting solution was slowly added to a magnetically stirred solution of 3-oxo-butyric acid methyl ester (17.4 gram, 0.15 mol) while keeping the temperature <5° C. After stirring the mixture for two hours water (120 ml) was added and the resulting mixture was extracted twice with diethyl ether. The combined organic layers were successively washed with water and a 5% aqueous NaHCO3 solution. The organic layer was dried over MgSO4, filtered and thoroughly concentrated to give crude 2-hydroxyimino-3-oxo-butyric acid methyl ester (24 gram) as a colorless oil which was not further purified. 1H-NMR (400 MHz, CDCl3): 2.42 (s, 3H), 3.91 (s, 3H), 9.90 (br s, 1H).

Workup

  1. customthe temperature <5° C
  2. additionwas added
  3. extractionthe resulting mixture was extracted twice with diethyl ether
  4. washThe combined organic layers were successively washed with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationthoroughly concentrated

Sources & evidence

ORD record
ord-12a9dd67f64d4103ae9b524a5dd81c39
Source dataset
uspto-grants-2015_01
Patent number
US08937184B2

Reaction notes

Loading…