Dimethylformamide → Ethyl 2-benzyloxyimino-3-oxobutyrate

HRID 745368Notes

Reaction equation

HRID 745368 reaction equation
[OH:1][N:2]=[C:3]([C:7](=[O:9])[CH3:8])[C:4]([O-:6])=[O:5].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[C:29](OCC)(=O)[CH3:30]>>[CH2:10]([O:1][N:2]=[C:3]([C:7](=[O:9])[CH3:8])[C:4]([O:6][CH2:29][CH3:30])=[O:5])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178468382HCID 178468382, compound

Product 1

HCID 53396355Ethyl 2-benzyloxyimino-3-oxobutyrate

Procedure

A mixture of 2-hydroxyimino-3-oxobutyrate (syn isomer, 47.1 g.), benzylbromide (61.6 g.), potassium carbonate (62.2 g.), N,N-dimethylformamide (70 ml.) and ethyl acetate (70 ml.) was treated in a similar manner to that of Example A-(1) to give ethyl 2-benzyloxyimino-3-oxobutyrate (syn isomer, 70.0 g.).

Workup

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

Sources & evidence

ORD record
ord-441b98744bb04c99a00ea682a8e04b57
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

Loading…