(E)-trifluoromethanesulfonic acid 2-[(hex-4-en-2-ynyl-trifluoromethanesulfonylamino)methyl]-6-(trimethylsilyl)phenyl ester

Base Information

• Chemical Name: (E)-trifluoromethanesulfonic acid 2-[(hex-4-en-2-ynyl-trifluoromethanesulfonylamino)methyl]-6-(trimethylsilyl)phenyl ester
• CAS No.: 866041-39-6
• Molecular Formula: C₁₈H₂₁F₆NO₅S₂Si
• Molecular Weight: 537.576
• Mol file: 866041-39-6.mol

Synonyms:(E)-trifluoromethanesulfonic acid 2-[(hex-4-en-2-ynyl-trifluoromethanesulfonylamino)methyl]-6-(trimethylsilyl)phenyl ester

Chemical Property of (E)-trifluoromethanesulfonic acid 2-[(hex-4-en-2-ynyl-trifluoromethanesulfonylamino)methyl]-6-(trimethylsilyl)phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-trifluoromethanesulfonic acid 2-[(hex-4-en-2-ynyl-trifluoromethanesulfonylamino)methyl]-6-(trimethylsilyl)phenyl ester

There total 6 articles about (E)-trifluoromethanesulfonic acid 2-[(hex-4-en-2-ynyl-trifluoromethanesulfonylamino)methyl]-6-(trimethylsilyl)phenyl 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: 74.0%

(E)-2-hex-4-en-2-ynylaminomethyl-6-(trimethylsilyl)phenol (866041-62-5) + trifluoromethylsulfonic anhydride (358-23-6) → (E)-trifluoromethanesulfonic acid 2-[(hex-4-en-2-ynyl-trifluoromethanesulfonylamino)methyl]-6-(trimethylsilyl)phenyl ester (866041-39-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/ol051372l

Reference yield:

2-[(prop-2-ynylamino)methyl]-6-(trimethylsilyl)phenol (866041-35-2) → (E)-trifluoromethanesulfonic acid 2-[(hex-4-en-2-ynyl-trifluoromethanesulfonylamino)methyl]-6-(trimethylsilyl)phenyl ester (866041-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / CuI; piperidine / (Ph₃P)2PdCl₂ / tetrahydrofuran / 0.5 h / 60 °C

2: 74 percent / (i-Pr₂)NEt / CH₂Cl₂ / 1 h / -78 °C

With piperidine; copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; 1: Sonogashira cross-coupling;

DOI:10.1021/ol051372l

Reference yield:

O-methoxymethylphenol (824-91-9) → (E)-trifluoromethanesulfonic acid 2-[(hex-4-en-2-ynyl-trifluoromethanesulfonylamino)methyl]-6-(trimethylsilyl)phenyl ester (866041-39-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / 0 °C

1.2: tetrahydrofuran; hexane / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 2 h / 0 °C

2.2: 87 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 97 percent / NaI; HCl / acetone; H₂O / 0.75 h / 55 °C

4.1: molecular sieves 3 Angstroem / methanol / 0.5 h / 20 °C

4.2: 83 percent / NaBH₄ / methanol / 1 h / 0 °C

5.1: 74 percent / CuI; piperidine / (Ph₃P)2PdCl₂ / tetrahydrofuran / 0.5 h / 60 °C

6.1: 74 percent / (i-Pr₂)NEt / CH₂Cl₂ / 1 h / -78 °C

With piperidine; hydrogenchloride; copper(l) iodide; n-butyllithium; 3 A molecular sieve; N-ethyl-N,N-diisopropylamine; sodium iodide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; 5.1: Sonogashira cross-coupling;

DOI:10.1021/ol051372l

upstream raw materials:

(E)-2-hex-4-en-2-ynylaminomethyl-6-(trimethylsilyl)phenol

trifluoromethylsulfonic anhydride

2-[(prop-2-ynylamino)methyl]-6-(trimethylsilyl)phenol

O-methoxymethylphenol