Dimethylformamide → Ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate

HRID 894749Notes

Reaction equation

HRID 894749 reaction equation
[OH:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12]([O:20][CH2:21][CH2:22]Br)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[C:12]([O:20][CH2:21][CH2:22][O:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5230902-Bromoethyl BenzoateHCID 178472877HCID 178472877, compound

Product 1

HCID 53765835Ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrateYield 92.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 15.7 g.), 2-bromoethyl benzoate (27.5 g.), potassium carbonate (20.7 g.), N,N-dimethylformamide (25 ml.) and ethyl acetate (25 ml.) was treated in a similar manner to that of Example A-(1) to give ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate (syn isomer, 28 g.).

Workup

  1. additionwas treated in a similar manner to that of Example A-(1)

Sources & evidence

ORD record
ord-53dc3ae120b0421f9b0504ed2738e154
Source dataset
uspto-grants-1981_08
Patent number
US04284631

Reaction notes

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