tert-Butyl ethyl methylpropanedioate

Base Information

• Chemical Name: tert-Butyl ethyl methylpropanedioate
• CAS No.: 56834-42-5
• Molecular Formula: C10H18O4
• Molecular Weight: 202.251
• DSSTox Substance ID: DTXSID90526729
• Nikkaji Number: J1.299.884H
• Mol file: 56834-42-5.mol

Synonyms:56834-42-5;tert-Butyl ethyl methylpropanedioate;1-tert-butyl 3-ethyl 2-methylmalonate;3-O-tert-butyl 1-O-ethyl 2-methylpropanedioate;tert-butyl ethyl methylmalonate;SCHEMBL1455828;DTXSID90526729;ALHHNDQKFRHCOJ-UHFFFAOYSA-N;1-(tert-Butyl) 3-ethyl 2-methylmalonate;F95239

Chemical Property of tert-Butyl ethyl methylpropanedioate

Chemical Property:

• PSA: 52.60000
• LogP: 1.52730
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 202.12050905
• Heavy Atom Count: 14
• Complexity: 215

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C(C)C(=O)OC(C)(C)C

Technology Process of tert-Butyl ethyl methylpropanedioate

There total 1 articles about tert-Butyl ethyl methylpropanedioate 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: 87.0%

monoethyl methylmalonate (2985-33-3) + tert-butyl alcohol (75-65-0) → 2-methylmalonic acid tert-butyl ester ethyl ester (56834-42-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 0.25h;

DOI:10.1021/jo0263824

Reference yield:

2-methylmalonic acid tert-butyl ester ethyl ester (56834-42-5) + 3-[2-chloro-4-(3-trifluoromethylphenylthio)phenyl]propyl methanesulfonate (1196866-18-8) → t-butyl ethyl 2-{3-[2-chloro-4-(3-trifluoromethylphenylthio)phenyl]propyl}-2-methyl-propane dioate (1196866-19-9)

Guidance literature:

2-methylmalonic acid tert-butyl ester ethyl ester; With sodium t-butanolate; In N,N-dimethyl-formamide; at 8 - 31 ℃; for 0.25h; Inert atmosphere; Industry scale;

3-[2-chloro-4-(3-trifluoromethylphenylthio)phenyl]propyl methanesulfonate; With sodium iodide; In N,N-dimethyl-formamide; at 50 - 56 ℃; for 3.5h; Inert atmosphere; Industry scale;

Reference yield:

2-methylmalonic acid tert-butyl ester ethyl ester (56834-42-5) → 1-(tert-butyl) 3-ethyl 2-methyl-2-(2-(2-tosylhydrazono)propanoyl)malonate

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / -78 - 55 °C / Cooling with ice; Inert atmosphere

1.2: 0.5 h / -78 - 20 °C / Inert atmosphere

2.1: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 18 h / 55 °C / Inert atmosphere

With dmap; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; mineral oil;

DOI:10.1021/acs.orglett.5b02847

upstream raw materials:

monoethyl methylmalonate

tert-butyl alcohol

Downstream raw materials:

ethyl hydrogen 2-{3-[2-chloro-4-(3-trifluoromethylphenylthio)phenyl]propyl}-2-methyl-propane dioate

C₂₂H₂₁ClF₃N₃O₃S

t-butyl ethyl 2-{3-[2-chloro-4-(3-trifluoromethylphenylthio)phenyl]propyl}-2-methyl-propane dioate

α-methylmalonate mono-tert-butyl ester