ethynyl(phenyl)carbamic acid tert-butyl ester

Base Information

• Chemical Name: ethynyl(phenyl)carbamic acid tert-butyl ester
• CAS No.: 1019202-25-5
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.268
• Mol file: 1019202-25-5.mol

Synonyms:ethynyl(phenyl)carbamic acid tert-butyl ester

Chemical Property of ethynyl(phenyl)carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethynyl(phenyl)carbamic acid tert-butyl ester

There total 6 articles about ethynyl(phenyl)carbamic acid tert-butyl ester 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: 94.0%

phenyl[(triisopropylsilanyl)ethynyl]carbamic acid tert-butyl ester (1019202-24-4) → ethynyl(phenyl)carbamic acid tert-butyl ester (1019202-25-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/j.tetlet.2008.01.073

Reference yield:

tert-butyl phenylcarbamate (3422-01-3) + bromoethyne (593-61-3) → ethynyl(phenyl)carbamic acid tert-butyl ester (1019202-25-5)

Guidance literature:

With potassium phosphate; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; In toluene; at 85 ℃; for 18h; Sealed tube;

DOI:10.1016/j.tetlet.2016.03.052

Reference yield:

tert-butyl phenylcarbamate (3422-01-3) → ethynyl(phenyl)carbamic acid tert-butyl ester (1019202-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(l) iodide; 1,10-Phenanthroline; potassium hexamethylsilazane / toluene / 90 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With copper(l) iodide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; toluene;

DOI:10.1002/ejoc.201301054

upstream raw materials:

phenyl[(triisopropylsilanyl)ethynyl]carbamic acid tert-butyl ester

tert-butyl phenylcarbamate

aniline

di-tert-butyl dicarbonate

Downstream raw materials:

N¹-isopropyl-N²-(4-methylbenzenesulfonyl)-2-[N-(1,1-dimethylethoxy)carbonyl-N-phenyl]aminoacetamidine

Refernces

• 1、 D'Hollander, Agathe C. A.,Romero, Eugénie,Vijayakumar, Kamsana,Le Houérou, Camille,Retailleau, Pascal,Dodd, Robert H.,Iorga, Bogdan I.,Cariou, Kevin. "Base-Mediated Generation of Ketenimines from Ynamides: [3+2] Annulation with Azaallyl Anions". supporting information. p. 2903 - 2908. Retrieved 2021/04/21.
• 2、 Tang, Luning,Huang, Hai,Xi, Yang,He, Guangke,Zhu, Hongjun. "Pd/Cu-Catalyzed tandem head-to-tail dimerization/cycloisomerization of terminal ynamides for the synthesis of 5-vinyloxazolones". . p. 2923 - 2930. Retrieved 2017/04/11.