2-Cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethanol

Base Information

• Chemical Name: 2-Cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethanol
• CAS No.: 169563-59-1
• Molecular Formula: C₁₆H₂₄O₃Si
• Molecular Weight: 292.45
• Mol file: 169563-59-1.mol

Synonyms:2-Cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethanol

Chemical Property of 2-Cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethanol

There total 8 articles about 2-Cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethanol 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: 84.0%

1-(tert-Butyldimethylsiloxy)-2-cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethane (169563-58-0) → 2-Cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethanol (169563-59-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1021/jo00126a030

Reference yield:

2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane (103477-58-3) → 2-Cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethanol (169563-59-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 56 percent / NaOMe / hexamethylphosphoric acid triamide / 6 h / Ambient temperature

2: 93 percent / p-TsOH, H₂O / acetone / 12 h / Heating

3: tetrahydrofuran; hexane / 1 h / 0 °C

4: PDC, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 0.17 h / Ambient temperature

6: aq. NaHCO₃, m-CPBA / CH₂Cl₂ / 1.5 h / Ambient temperature

7: 54 percent / NaH / tetrahydrofuran / 1.) 65 deg C, 10 h, 2.) 65 deg C, 3 h

8: 84 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

With dipyridinium dichromate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; sodium methylate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetone;

DOI:10.1021/jo00126a030

Reference yield:

4-Acetyl-5-(trimethylsilyl)veratrole (169563-56-8) → 2-Cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethanol (169563-59-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 0.17 h / Ambient temperature

2: aq. NaHCO₃, m-CPBA / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 54 percent / NaH / tetrahydrofuran / 1.) 65 deg C, 10 h, 2.) 65 deg C, 3 h

4: 84 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

With tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00126a030

upstream raw materials:

1-(tert-Butyldimethylsiloxy)-2-cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethane

2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane

4,5-dimethoxy-2-(trimethylsilyl)benzaldehyde

4-Acetyl-5-(trimethylsilyl)veratrole