Ethyl 6-oxo-6-(3-thienyl)hexanoate

Base Information

• Chemical Name: Ethyl 6-oxo-6-(3-thienyl)hexanoate
• CAS No.: 333355-34-3
• Molecular Formula: C₁₂H₁₆O₃S
• Molecular Weight: 240.323
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80463053
• Nikkaji Number: J1.456.124B
• Wikidata: Q82287782
• Mol file: 333355-34-3.mol

Synonyms:ETHYL 6-OXO-6-(3-THIENYL)HEXANOATE;333355-34-3;ethyl 6-oxo-6-thiophen-3-ylhexanoate;MFCD07699060;DTXSID80463053;AKOS016018822;MS-21546;ETHYL6-OXO-6-(3-THIENYL)HEXANOATE;ETHYL 6-OXO-6-(THIOPHEN-3-YL)HEXANOATE

Chemical Property of Ethyl 6-oxo-6-(3-thienyl)hexanoate

Chemical Property:

• Vapor Pressure: 6.73E-05mmHg at 25°C
• Boiling Point: 344.1°C at 760 mmHg
• Flash Point: 161.9°C
• PSA: 71.61000
• Density: 1.128g/cm³
• LogP: 3.05430
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 240.08201554
• Heavy Atom Count: 16
• Complexity: 240

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl6-oxo-6-(3-thienyl)hexanoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCCCC(=O)C1=CSC=C1

Technology Process of Ethyl 6-oxo-6-(3-thienyl)hexanoate

There total 3 articles about Ethyl 6-oxo-6-(3-thienyl)hexanoate 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: 67.0%

(5-ethoxy-5-oxopentyl)zinc(II) iodide (109976-46-7) + thiophene-3-carbothioic acid S-ethyl ester → ethyl 6-oxo-6-(3-thienyl)hexanoate (333355-34-3)

Guidance literature:

With N,N-dimethyl-formamide; palladium on activated charcoal; In tetrahydrofuran; toluene; at 25 ℃; for 22h;

DOI:10.1016/S0040-4039(00)01984-5

Reference yield: 61.0%

ethyl 5-iodopentanoate (41302-32-3) + thiophene-3-carbothioic acid S-ethyl ester → ethyl 6-oxo-6-(3-thienyl)hexanoate (333355-34-3)

Guidance literature:

ethyl 5-iodopentanoate; With chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; at 55 - 60 ℃; for 0.5h;

thiophene-3-carbothioic acid S-ethyl ester; 10percent Pd(OH)2/C; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; at 25 ℃; for 68h; Further stages.;

DOI:10.1021/jo0265277

Reference yield:

ethyl 5-iodopentanoate (41302-32-3) → ethyl 6-oxo-6-(3-thienyl)hexanoate (333355-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ethylene dibromide / tetrahydrofuran / 0.05 h / 65 °C / Inert atmosphere

1.2: 0.25 h / 25 °C / Inert atmosphere

1.3: 2 h / 55 - 60 °C / Inert atmosphere

2.1: 5% Pd(OH)₂/C; N,N-dimethyl-formamide / tetrahydrofuran; toluene / 68 h / 25 - 35 °C / Inert atmosphere

With 5% Pd(OH)₂/C; ethylene dibromide; N,N-dimethyl-formamide; In tetrahydrofuran; toluene; 2.1: |Fukuyama Coupling;

DOI:10.15227/orgsyn.084.0285

upstream raw materials:

(5-ethoxy-5-oxopentyl)zinc(II) iodide

ethyl 5-iodopentanoate

Refernces

• 1、 Mori, Yoshikazu,Seki, Masahiko,Aoyama, Naohiro,Shibasaki, Masakatsu. "Synthesis of multi-functionalized ketones through the fukuyama coupling reaction catalyzed by pearlman’s catalyst: Preparation of ethyl 6-oxotridecanoate: (Tridecanoic acid, 6-oxo-, ethyl ester)". . p. 285 - 294. Retrieved 2017/10/06.