Propargyl bromide → Ethyl 2-propargyloxyimino-3-oxobutyrate

HRID 27265Notes

Reaction equation

HRID 27265 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)[C:19]#[CH:20]>CN(C)C=O>[CH2:20]([O:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:19]#[CH:18]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 178472877HCID 178472877, compound

Product 1

HCID 53965351Ethyl 2-propargyloxyimino-3-oxobutyrateYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 56.7 g), N,N-dimethylformamide (280 ml), potassium carbonate (72.3 g) and propargyl bromide (43 g) was stirred at room temperature for 4 hrs. The reaction mixture was treated in a conventional manner to give ethyl 2-propargyloxyimino-3-oxobutyrate (syn isomer, 71.2 g).

Workup

  1. additionThe reaction mixture was treated in a conventional manner

Sources & evidence

ORD record
ord-cb2284ce402f41e1b6a42a923dcdd498
Source dataset
uspto-grants-1980_09
Patent number
US04220761

Reaction notes

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