2-(2-Phenylethyl)-4-methylenetetrahydrofuran

Base Information

• Chemical Name: 2-(2-Phenylethyl)-4-methylenetetrahydrofuran
• CAS No.: 77862-52-3
• Molecular Formula: C₁₃H₁₆O
• Molecular Weight: 188.269
• Mol file: 77862-52-3.mol

Synonyms:2-(2-Phenylethyl)-4-methylenetetrahydrofuran

Chemical Property of 2-(2-Phenylethyl)-4-methylenetetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-Phenylethyl)-4-methylenetetrahydrofuran

There total 10 articles about 2-(2-Phenylethyl)-4-methylenetetrahydrofuran 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: 99.0%

3-phenyl-propionaldehyde (104-53-0) + [2-(acetoxymethyl)prop-2-enyl]trimethylsilane (72047-94-0) → 2-(2-Phenylethyl)-4-methylenetetrahydrofuran (77862-52-3)

Guidance literature:

trimethyltin acetate; palladium diacetate; triphenylphosphine; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/ja00197a060

Reference yield: 72.0%

3-phenyl-propionaldehyde (104-53-0) + methylene cyclopropane (6142-73-0) → 2-(2-Phenylethyl)-4-methylenetetrahydrofuran (77862-52-3) + 5-Chloromethyl-1-phenyl-hex-5-en-3-ol

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1016/S0040-4039(97)00981-7

Reference yield: 68.0%

rac-1-phenyl-5-((trimethylsilyl)methyl)hex-5-en-3-ol (84212-96-4) → 2-(2-Phenylethyl)-4-methylenetetrahydrofuran (77862-52-3)

Guidance literature:

With iodosylbenzene; boron trifluoride diethyl etherate; In 1,4-dioxane; for 2h; Ambient temperature;

upstream raw materials:

3-phenyl-propionaldehyde

[2-(acetoxymethyl)prop-2-enyl]trimethylsilane

6-(Dimethylamino)-5-methylene-1-phenylhexan-3-ol

rac-1-phenyl-5-((trimethylsilyl)methyl)hex-5-en-3-ol

Refernces

• 1、 Trost, Barry M.,King, Steven A.,Schmidt, Thomas. "Palladium-Catalyzed Trimethylenemethane Reaction To Form Methylenetetrahydrofurans. Aldehyde and Ketone Substrates and the Tin Effect". . p. 5902 - 5915. Retrieved 2007/10/02.
• 2、 Ochiai, Masahito,Fujita, Eiichi,Arimoto, Masao,Yamaguchi, Hideo. "Iodine(III)-Mediated Intramolecular Cyclization of Hydroxy Allylsilanes: Synthesis of 5- or 6-Membered β-Methylene Cyclic Ethers". . p. 989 - 997. Retrieved 2007/10/02.