Ethyl 4-chloroacetoacetate → Ethyl 4-ethoxy-3-oxobutyrate

HRID 1284981Notes

Reaction equation

HRID 1284981 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]([CH2:8]Cl)=[O:7])[CH3:2].[CH3:11][CH2:12][O-:13].[Na+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]([CH2:8][O:13][CH2:12][CH3:11])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 2723922Sodium ethoxide

Product 1

HCID 3016245Ethyl 4-ethoxy-3-oxobutyrateYield 90.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the method described in Example 1, 108.6 g of 4-chloroacetoacetic acid ethyl ester in 143 g of acetonitrile was reacted with 103.6 g of sodium ethylate. 4-ethoxyacetoacetic acid ethyl ester was obtained in a yield of 90.4 percent, related to the amount of 4-chloroacetoacetic acid ethyl ester used. The purity of the product was 98.5 percent.

Sources & evidence

ORD record
ord-69497f0993274c4eb908dcf6b6e051e5
Source dataset
uspto-grants-1986_01
Patent number
US04564696

Reaction notes

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