(E)-tert-butyl 4-acetoxybut-2-enoate

Base Information

• Chemical Name: (E)-tert-butyl 4-acetoxybut-2-enoate
• CAS No.: 902154-51-2
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.235
• Hs Code.: 2917198090
• DSSTox Substance ID: DTXSID50469481
• Nikkaji Number: J2.187.078A,J2.324.199D
• Mol file: 902154-51-2.mol

Synonyms:(E)-tert-butyl 4-acetoxybut-2-enoate;902154-51-2;Tert-butyl (E)-4-acetyloxybut-2-enoate;TERT-BUTYL 4-ACETOXYBUT-2-ENOATE;(E)-tert-butyl4-acetoxybut-2-enoate;SCHEMBL16140917;SCHEMBL18092961;DTXSID50469481;CLB15451;(E)-t-Butyl 4-acetoxybut-2-enoate;MFCD11976615;AKOS015841030;WS-00512;D86360

Chemical Property of (E)-tert-butyl 4-acetoxybut-2-enoate

Chemical Property:

• Vapor Pressure: 0.012mmHg at 25°C
• Boiling Point: 260.207°C at 760 mmHg
• Flash Point: 120.711°C
• PSA: 52.60000
• Density: 1.031g/cm³
• LogP: 1.44740
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 200.10485899
• Heavy Atom Count: 14
• Complexity: 235

Purity/Quality:

99.3% ^*data from raw suppliers

(E)-tert-Butyl4-acetoxybut-2-enoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC=CC(=O)OC(C)(C)C
• Isomeric SMILES: CC(=O)OC/C=C/C(=O)OC(C)(C)C

Technology Process of (E)-tert-butyl 4-acetoxybut-2-enoate

There total 2 articles about (E)-tert-butyl 4-acetoxybut-2-enoate 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: 58.0%

(E)-tert-butyl 4-bromobut-2-enoate (86606-04-4) + potassium acetate (127-08-2) → γ-acetoxycrotonic acid tert-butyl ester (902154-51-2)

Guidance literature:

In acetonitrile; at 20 - 60 ℃; for 4h;

Reference yield:

tert-butyl (E)-crotonate (79218-15-8) → γ-acetoxycrotonic acid tert-butyl ester (902154-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NBS; AIBN / CCl₄ / 3 h / Heating

2: 1.68 g / dimethylformamide / 14 h / 0 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1002/adsc.200505149

Reference yield:

γ-acetoxycrotonic acid tert-butyl ester (902154-51-2) → (S)-tert-butyl 3-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)-4-((R)-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)butanoate

Guidance literature:

Multi-step reaction with 3 steps

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dichloromethane / 0.25 h / Inert atmosphere

1.2: 24 h / Inert atmosphere

2.1: potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 1.17 h / 90 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; palladium 10% on activated carbon; hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; potassium hydroxide; In 1,4-dioxane; ethanol; dichloromethane;

upstream raw materials:

(E)-tert-butyl 4-bromobut-2-enoate

potassium acetate

tert-butyl (E)-crotonate

Refernces

• 1、 Anderson, Niall A.,Campbell, Ian B.,Fallon, Brendan J.,Lynn, Sean M.,Macdonald, Simon J. F.,Pritchard, John M.,Procopiou, Panayiotis A.,Sollis, Steven L.,Thorp, Lee R.. "Synthesis and determination of absolute configuration of a non-peptidic αvβ6 integrin antagonist for the treatment of idiopathic pulmonary fibrosis". . p. 5992 - 6009. Retrieved 2016/07/06.
• 2、 Nemoto, Tetsuhiro,Fukuda, Tomoaki,Matsumoto, Takayoshi,Hitomi, Tsukasa,Hamada, Yasumasa. "Enantioselective construction of all-carbon quaternary stereocenters using palladium-catalyzed asymmetric allylic alkylation of γ-acetoxy-α, β-unsaturated carbonyl compounds". . p. 1504 - 1506. Retrieved 2007/10/03.