N-(6-(tert-butyldimethylsilyloxy)-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline

Base Information

• Chemical Name: N-(6-(tert-butyldimethylsilyloxy)-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline
• CAS No.: 447454-35-5
• Molecular Formula: C₂₀H₃₀F₄N₄OSi
• Molecular Weight: 446.564
• Mol file: 447454-35-5.mol

Synonyms:N-(6-(tert-butyldimethylsilyloxy)-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline

Chemical Property of N-(6-(tert-butyldimethylsilyloxy)-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(6-(tert-butyldimethylsilyloxy)-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline

There total 5 articles about N-(6-(tert-butyldimethylsilyloxy)-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline 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: 60.0%

E-1-(tert-butyldimethylsilyloxy)-3-methyl-hex-2-en-6-al (447454-31-1) + N-methyl-4-azidotetrafluoroaniline (447454-34-4) → N-(6-(tert-butyldimethylsilyloxy)-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline (447454-35-5)

Guidance literature:

N-methyl-4-azidotetrafluoroaniline; With pyridine; titanium tetrachloride; In dichloromethane; toluene; at -78 ℃; for 0.0833333h;

E-1-(tert-butyldimethylsilyloxy)-3-methyl-hex-2-en-6-al; In dichloromethane; toluene; at 20 ℃;

With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; toluene; at 20 ℃; for 20h; Further stages.;

DOI:10.1021/ja0124717

Reference yield:

4-(N-(tert-butoxycarbonyl)amino)tetrafluorophenyl azide (294187-76-1) → N-(6-(tert-butyldimethylsilyloxy)-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline (447454-35-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 93 percent / tetrahydrofuran / 5 °C

2.1: HCl; AcOH / CH₂Cl₂ / 0 - 20 °C

3.1: pyridine; TiCl₄ / CH₂Cl₂; toluene / 0.08 h / -78 °C

3.2: CH₂Cl₂; toluene / 20 °C

3.3: 60 percent / NaBH(OAc)3; glacial acetic acid / CH₂Cl₂; toluene / 20 h / 20 °C

With pyridine; hydrogenchloride; titanium tetrachloride; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja0124717

Reference yield:

(E)-6-(tert-butyldimethylsilyloxy)-4-methylhex-4-en-1-ol (447454-30-0) → N-(6-(tert-butyldimethylsilyloxy)-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline (447454-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 66 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.75 h / -78 - -20 °C

2.1: pyridine; TiCl₄ / CH₂Cl₂; toluene / 0.08 h / -78 °C

2.2: CH₂Cl₂; toluene / 20 °C

2.3: 60 percent / NaBH(OAc)3; glacial acetic acid / CH₂Cl₂; toluene / 20 h / 20 °C

With pyridine; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 1.1: Swern oxidation;

DOI:10.1021/ja0124717

upstream raw materials:

E-1-(tert-butyldimethylsilyloxy)-3-methyl-hex-2-en-6-al

N-methyl-4-azidotetrafluoroaniline

4-(N-(tert-butoxycarbonyl)amino)tetrafluorophenyl azide

(E)-6-(tert-butyldimethylsilyloxy)-4-methylhex-4-en-1-ol

Downstream raw materials:

(E)-N-(6-chloro-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline