1-Bromopentane → Ethyl 3-oxo-2-[(pentyloxy)imino]butanoate

HRID 1284701Notes

Reaction equation

HRID 1284701 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(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH3:22]>CN(C)C=O>[CH2:18]([O:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 178472877HCID 178472877, compound

Product 1

HCID 53697317Ethyl 3-oxo-2-[(pentyloxy)imino]butanoateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 40 g.), N,N-dimethylformamide (200 ml.), potassium carbonate (52 g.) and pentyl bromide (37.9 g.) were treated in a similar manner to that of Example F-(1) to give ethyl 2-pentyloxyimino-3-oxobutyrate (syn isomer, 57.5 g.), oil.

Sources & evidence

ORD record
ord-4cdb7af8fc40492a917287a0cc1245ce
Source dataset
uspto-grants-1986_01
Patent number
US04563522

Reaction notes

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