Water → Diethyl 2-ethoxycarbonyloxyiminomalonate

HRID 1283751Notes

Reaction equation

HRID 1283751 reaction equation
[OH:1][N:2]=[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].O.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])O.[Na+]>CC(C)=O>[CH2:19]([O:18][C:16]([O:1][N:2]=[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 6399380Diethyl (hydroxyimino)malonate

Product 1

HCID 20567995Diethyl 2-ethoxycarbonyloxyiminomalonateYield 101.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of diethyl 2-hydroxyiminomalonate (18.9 g), water (50 ml) and acetone (8 ml) is cooled at 0°C, and ethyl chloroformate (9.8 g) is dropwise added thereto. The resulting mixture is, after adjusted to pH 7 to 8 with the addition of an aqueous solution of sodium hydrogencarbonate, stirred at room temperature for 4 hours. The reaction mixture is extracted with ether, and the ether layer is washed with an aqueous solution of sodium chloride, dried and concentrated to give diethyl 2-ethoxycarbonyloxyiminomalonate (24 g) as an oil.

Workup

  1. extractionThe reaction mixture is extracted with ether
  2. washthe ether layer is washed with an aqueous solution of sodium chloride
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-03b5619f8c8840129fa6e04404648d1c
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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