(3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one

Base Information

• Chemical Name: (3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one
• CAS No.: 808739-71-1
• Molecular Formula: C₁₈H₂₈O₂Si
• Molecular Weight: 304.505
• Mol file: 808739-71-1.mol

Synonyms:(3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one

Chemical Property of (3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one

There total 1 articles about (3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one 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: 80.0%

acetonyltriphenylphosphonium chloride (1235-21-8) + 3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde (147974-20-7) → (3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one (808739-71-1)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In toluene; for 2h; Heating;

DOI:10.1055/s-2004-831240

Reference yield: 90.0%

sodium 4-methylbenzenesulfinate (824-79-3) + (3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one (808739-71-1) → 6-[4-(tert-butyldimethylsilyloxy)phenyl]-4-[(4-methylphenyl)sulfonyl]hexan-2-one (808739-72-2)

Guidance literature:

With acetic acid; In ethanol; at 20 ℃; for 48h;

DOI:10.1055/s-2004-831240

Reference yield:

(3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one (808739-71-1) → 3-[2-(4-tert-butyldimethylsilyloxy)phenyl]ethyl-5-hydroxycyclohex-2-enone (808740-95-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / AcOH / ethanol / 48 h / 20 °C

2.1: 80 percent / p-TsOH / toluene / 2.5 h / Heating

3.1: t-BuLi / hexane; tetrahydrofuran / 0.33 h / 0 °C

3.2: 75 percent / hexane; tetrahydrofuran / 12 h / 20 °C

4.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

4.2: 80 percent / AcOH; Zn / CH₂Cl₂ / 2 h / 20 °C

5.1: 55 percent / BF₃*OEt₂ / CH₂Cl₂ / 15 h / -20 °C

6.1: 100 percent / aq. CaCO₃; HgCl₂; AgNO₃ / acetonitrile / 1 h / 60 °C

7.1: 45 percent / K₂CO₃ / methanol / 3 h / 0 °C

With boron trifluoride diethyl etherate; tert.-butyl lithium; potassium carbonate; toluene-4-sulfonic acid; ozone; silver nitrate; acetic acid; calcium carbonate; mercury dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; acetonitrile;

DOI:10.1055/s-2004-831240

upstream raw materials:

acetonyltriphenylphosphonium chloride

3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde

Downstream raw materials:

6-[4-(tert-butyldimethylsilyloxy)phenyl]-4-[(4-methylphenyl)sulfonyl]hexan-2-one

3-[2-(4-tert-butyldimethylsilyloxy)phenyl]ethyl-5-hydroxycyclohex-2-enone

2-({4-[4-(tert-butyldimethylsilyloxy)phenyl]}-2-[(4-methylphenyl)sulfonyl]butyl)-2-methyl-1,3-dioxolane

3-{2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}-5-oxo-3-[(4-methylphenyl)sulfonyl]hexanal