Methyl 4-(methylsulfanyl)-3-oxobutanoate

Base Information

• Chemical Name: Methyl 4-(methylsulfanyl)-3-oxobutanoate
• CAS No.: 64127-51-1
• Molecular Formula: C6H10O3S
• DSSTox Substance ID: DTXSID80565884
• Wikidata: Q82451207
• Mol file: 64127-51-1.mol

Synonyms:64127-51-1;Methyl 4-(methylsulfanyl)-3-oxobutanoate;SCHEMBL5731252;DTXSID80565884;EN300-1846267

Chemical Property of Methyl 4-(methylsulfanyl)-3-oxobutanoate

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 162.03506535
• Heavy Atom Count: 10
• Complexity: 133

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(=O)CSC

Technology Process of Methyl 4-(methylsulfanyl)-3-oxobutanoate

There total 1 articles about Methyl 4-(methylsulfanyl)-3-oxobutanoate 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:

ethyl (2-chloroaceto)acetate (638-07-3) + sodium thiomethoxide (5188-07-8) → 4-methylthioacetoacetic acid ethyl ester (14109-74-1) + 4-(methylthio)-3-oxobutanoic acid methyl ester (64127-51-1)

Guidance literature:

In methanol; at 5 - 20 ℃; for 18h;

Reference yield: 54.0%

4-(methylthio)-3-oxobutanoic acid methyl ester (64127-51-1) + 4-chloro-aniline (106-47-8) → (5-chloro-3-methylsulfanyl-1H-indol-2-yl)-acetic acid methyl ester (573716-46-8) + methylsulfanyl-acetone (14109-72-9)

Guidance literature:

Reference yield:

4-(methylthio)-3-oxobutanoic acid methyl ester (64127-51-1) → *-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ4-isothiazole-4-acetic acid benzyl ester (144373-39-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) conc. HCl, 2.) conc. HCl, 3.) 3 N aq. HCl

2: 61 percent / K₂CO₃ / dimethylformamide / 18 h / 60 °C

3: 31 percent / O₃, Sudan III / CH₂Cl₂ / -78 °C

4: 49 percent / O-(mesitylsulfonyl)hydroxylamine / CH₂Cl₂ / 18 h / 25 °C

5: 100 percent / ethanol; H₂O / Heating

With hydrogenchloride; oil scarlet; mesitylenesulfonylhydroxylamine; potassium carbonate; ozone; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00104a014

upstream raw materials:

ethyl (2-chloroaceto)acetate

sodium thiomethoxide

Downstream raw materials:

*-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ⁴-isothiazole-4-acetic acid benzyl ester

2-hydroxy-2-<(methylthio)methyl>butanedioic acid dibenzyl ester

*,S^*)>-2-hydroxy-2-<(methylsulfinyl)methyl>butanedioic acid dibenzyl ester

*,R^*)>-2-hydroxy-2-<(methylsulfinyl)methyl>butanedioic acid dibenzyl ester