Ethyl 4-acetoxyacetoacetate

Base Information

• Chemical Name: Ethyl 4-acetoxyacetoacetate
• CAS No.: 35594-15-1
• Molecular Formula: C8H12O5
• Molecular Weight: 188.18
• DSSTox Substance ID: DTXSID40467214
• Nikkaji Number: J1.782.713H
• Wikidata: Q82294025
• Mol file: 35594-15-1.mol

Synonyms:35594-15-1;ethyl 4-acetoxyacetoacetate;ethyl 4-acetoxy-3-oxobutanoate;ethyl 4-acetyloxy-3-oxobutanoate;Ethyl 4-(acetyloxy)-3-oxobutanoate;ethyl 4-acetoxy-acetoacetate;ethyl4-acetoxy-3-oxobutanoate;SCHEMBL561195;Ethyl 4-acetoxy-3-oxobutyrate;ethyl 4-acetoxy-3-oxo-butyrate;DTXSID40467214;CYNVCBUVDFHONF-UHFFFAOYSA-N;ethyl 4-(acetoxy)-3-oxobutanoate;3-Oxo-4-acetoxybutyric acid ethyl ester;gamma-acetoxyacetoacetic acid ethyl ester;gamma-acetoxy-acetoacetic acid ethyl ester;FT-0729542

Chemical Property of Ethyl 4-acetoxyacetoacetate

Chemical Property:

• PSA: 69.67000
• LogP: 0.07180
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane; Ethyl Acetate; Methanol
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 188.06847348
• Heavy Atom Count: 13
• Complexity: 209

Purity/Quality:

99% ^*data from raw suppliers

Ethyl4-Acetoxy-3-oxobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)COC(=O)C
• Uses: Ethyl 4-Acetoxy-3-oxobutanoate is an intermediate used in the synthesis of Dehydro Felodipine Ester Lactone (D229690), which is a metabolite of Felodipine (F232375).

Technology Process of Ethyl 4-acetoxyacetoacetate

There total 18 articles about Ethyl 4-acetoxyacetoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

ethyl 4-acetoxybut-2-ynoate (1246080-11-4) → ethyl 4-acetoxyacetoacetate (35594-15-1)

Guidance literature:

With (triphenylphosphine)gold(I) chloride; water; silver trifluoromethanesulfonate; In 1,4-dioxane; at 20 ℃; for 1h; Reagent/catalyst; Solvent; Time; Concentration; regioselective reaction;

DOI:10.1021/acs.joc.5b00400

Reference yield: 53.0%

ethyl (2-chloroaceto)acetate (638-07-3) + potassium acetate (127-08-2) → ethyl 4-acetoxyacetoacetate (35594-15-1)

Guidance literature:

In acetic acid; at 90 ℃; for 18h;

DOI:10.1021/jo201822k

Reference yield: 27.0%

ethyl (2-chloroaceto)acetate (638-07-3) + sodium acetate (127-09-3) → ethyl 4-acetoxyacetoacetate (35594-15-1)

Guidance literature:

With acetic acid; at 95 ℃; for 16h;

DOI:10.1039/c6nj02048h

upstream raw materials:

ethyl 4-diazo-3-oxobutyrate

acetic acid

4-bromoethyl acetoacetate

sodium acetate

Downstream raw materials:

2-Acetoxymethyl-4,6-dihydroxy-benzoic acid ethyl ester

DL-2-(hydroxymethyl)aspartic acid

4-hydroxy-2(5H)-furanone

3-ethyl 5-isopropyl 2-acetoxymethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate