1,3-Diethyl 2-oxopropanedioate → HCID 18755336, compound

HRID 1838613Notes

Reaction equation

HRID 1838613 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5](=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH2:13]([O:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH2:13]([O:20][N:21]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 102313O-Benzylhydroxylamine

Product 1

HCID 18755336HCID 18755336, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
75 °C

Procedure

Di-ethylketomalonate (60 g) was added at 20° C. to a stirred suspension of O-benzylhydroxylamine (57.8 g) in IMS (500 ml) containing pyridine (30 ml). The reaction was heated at 75° C. for 4 hr. The reaction was cooled and solvents removed under reduced pressure. The residue was partitioned between EtOAc (500 ml) and water (300 ml) and the organic layer separated, washed with water (250 ml) and dried over MgSO4. Solvents were evaporated to give the title compound 95.3 g, as a colourless oil (99% th, ca 3% w/w residual EtOAc) which was used without further purification.

Workup

  1. temperatureThe reaction was cooled
  2. customsolvents removed under reduced pressure
  3. customThe residue was partitioned between EtOAc (500 ml) and water (300 ml)
  4. customthe organic layer separated
  5. washwashed with water (250 ml)
  6. dry with materialdried over MgSO4
  7. customSolvents were evaporated

Sources & evidence

ORD record
ord-f8a7e771715a4cf2b299e12a277f70a9
Source dataset
uspto-grants-2004_01
Patent number
US06673921B2

Reaction notes

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