(E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-3-(methoxyacetoxy)cyclodeca-1,5-diyne

Base Information

• Chemical Name: (E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-3-(methoxyacetoxy)cyclodeca-1,5-diyne
• CAS No.: 736156-55-1
• Molecular Formula: C₂₇H₃₆O₄Si
• Molecular Weight: 452.666
• Mol file: 736156-55-1.mol

Synonyms:(E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-3-(methoxyacetoxy)cyclodeca-1,5-diyne

Chemical Property of (E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-3-(methoxyacetoxy)cyclodeca-1,5-diyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-3-(methoxyacetoxy)cyclodeca-1,5-diyne

There total 4 articles about (E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-3-(methoxyacetoxy)cyclodeca-1,5-diyne 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: 52.0%

(E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]cyclodeca-1,5-diyn-3-ol (736156-53-9) + 2-methoxyacetic acid (625-45-6) → (E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-3-(methoxyacetoxy)cyclodeca-1,5-diyne (736156-55-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1016/j.bmc.2005.12.040

Reference yield:

(E)-2-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-10-iododeca-3,9-diynal (736156-60-8) → (E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-3-(methoxyacetoxy)cyclodeca-1,5-diyne (736156-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 24 percent / CrCl₂; NiCl₂ / tetrahydrofuran / 8 h / 20 °C

2: 52 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 72 h / 20 °C

With chromium dichloride; dmap; dicyclohexyl-carbodiimide; nickel dichloride; In tetrahydrofuran; dichloromethane; 1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1016/j.bmc.2005.12.040

Reference yield:

2-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]deca-3,9-diyn-1-ol → (E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-3-(methoxyacetoxy)cyclodeca-1,5-diyne (736156-55-1)

Guidance literature:

Multi-step reaction with 4 steps

1: iodine; morpholine / toluene / 18 h / 60 °C

2: 100 percent / pyridinium dichromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 20 °C

3: 24 percent / CrCl₂; NiCl₂ / tetrahydrofuran / 8 h / 20 °C

4: 52 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 72 h / 20 °C

With morpholine; chromium dichloride; dmap; dipyridinium dichromate; 4 A molecular sieve; iodine; dicyclohexyl-carbodiimide; nickel dichloride; In tetrahydrofuran; dichloromethane; toluene; 3: Nozaki-Hiyama-Kishi reaction;

DOI:10.1016/j.bmc.2005.12.040

upstream raw materials:

(E)-4-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]cyclodeca-1,5-diyn-3-ol

2-methoxyacetic acid

(E)-2-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-10-iododeca-3,9-diynal

(E)-2-[2'-(tert-butyldimethylsilyloxy)-1'-phenylethylidene]-10-iododeca-3,9-diyn-1-ol