methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane

Base Information

• Chemical Name: methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane
• CAS No.: 35453-05-5
• Molecular Formula: C₁₀H₁₂OS₂
• Molecular Weight: 212.337
• Mol file: 35453-05-5.mol

Synonyms:methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane

Chemical Property of methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane

There total 5 articles about methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane 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: 91.0%

benzaldehyde (100-52-7) + methyl methylsulfinylmethyl sulfide (33577-16-1) → methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane (35453-05-5)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; at 60 ℃; for 6h; stereoselective reaction; Inert atmosphere;

DOI:10.1246/bcsj.20130148

Reference yield:

methyl phenyldithioacetate (2168-85-6) + methyl iodide (74-88-4) → (Z)-α-(methylthio)styryl methyl sulfoxide (35453-10-2) + methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane (35453-05-5)

Guidance literature:

methyl phenyldithioacetate; With methyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.25h;

With rac N-phenylsulfonyl tert-butyl methyl oxaziridine; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.333333h;

methyl iodide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 5h;

DOI:10.1021/jo0492362

Reference yield:

benzaldehyde (100-52-7) → (Z)-α-(methylthio)styryl methyl sulfoxide (35453-10-2) + methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane (35453-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium

2: potassium tert-butylate / toluene; tert-butyl alcohol

With n-butyllithium; potassium tert-butylate; In toluene; tert-butyl alcohol;

DOI:10.1246/bcsj.20140241

upstream raw materials:

benzaldehyde

methyl methylsulfinylmethyl sulfide

methyl phenyldithioacetate

methyl iodide

Downstream raw materials:

2-(methylsulfanyl)-3-phenylbenzofuran

2-butyl-3-phenylbenzofuran

2-benzyl-3-phenylbenzofuran

2-methyl-3-phenylbenzofuran

Refernces

• 1、 Murakami, Kei,Yorimitsu, Hideki,Osuka, Atsuhiro. "Two-step, practical, and diversity-oriented synthesis of multisubstituted benzofurans from phenols through Pummerer annulation followed by cross-coupling". . p. 1349 - 1366. Retrieved 2015/02/19.
• 2、 Hewson, Alan T.,Richardson, Stewart K.,Sharpe, David A.. "Acid Catalysed Reactions of Aryl Ketene Dithioacetal S-Oxides: Synthesis of Chloroketene Thioacetals and Thioesters". . p. 2967 - 2970. Retrieved 2007/10/02.