Benzofuran, 2,3-dihydro-3-methylene-

Base Information

• Chemical Name: Benzofuran, 2,3-dihydro-3-methylene-
• CAS No.: 36638-16-1
• Molecular Formula: C9H8O
• Molecular Weight: 132.162
• Mol file: 36638-16-1.mol

Synonyms:

Chemical Property of Benzofuran, 2,3-dihydro-3-methylene-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzofuran, 2,3-dihydro-3-methylene-

There total 10 articles about Benzofuran, 2,3-dihydro-3-methylene- 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: 51.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (2-hydroxybenzyl)triphenylphosphonium bromide (70340-04-4) → 2,3-dihydro-3-methylenebenzofuran (36638-16-1) + 2-allylphenol (695-84-1)

Guidance literature:

(2-hydroxybenzyl)triphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

formaldehyd; In tetrahydrofuran; for 5h; Heating;

DOI:10.1246/bcsj.78.2209

Reference yield: 17.0%

2-(prop-2-yn-1-yloxy)benzenediazonium tetrafluoroborate → 3-methyl-benzofuran (21535-97-7) + 3-hydroxymethylbenzofuran (4687-23-4) + 2,3-dihydro-3-methylenebenzofuran (36638-16-1)

Guidance literature:

β‐cyclodextrin; In water; at 25 ℃; presence of air (oxygen);

DOI:10.1246/cl.1991.337

Reference yield: 16.0%

1-allyloxy-2-iodobenzene (24892-63-5) → 3-methyl-benzofuran (21535-97-7) + 2,3-dihydro-3-methylenebenzofuran (36638-16-1) + C9H9IO

Guidance literature:

With palladium diacetate; tetramethlyammonium chloride; sodium carbonate; 1,4-di(diphenylphosphino)-butane; phenylboronic acid; In water; toluene; at 110 ℃; for 2h; Reagent/catalyst; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201310275

upstream raw materials:

1-allyloxy-2-iodobenzene

1-iodo-2-(2-propynyloxy)benzene

formaldehyd

(2-hydroxybenzyl)triphenylphosphonium bromide

Downstream raw materials:

3-methyl-benzofuran

3-(2-phenylethyl)benzofuran

(R)-3-(2-(5,5-diphenyltetrahydrofuran-2-yl)ethyl)benzofuran

Refernces

Cycloisomerization promoted by the combination of a ruthenium-carbene catalyst and trimethylsilyl vinyl ether, and its application in the synthesis of heterocyclic compounds: 3-Methylene-2,3-dihydroindoles and 3-methylene-2,3- dihydrobenzofurans

10.1002/anie.200454157

The study focuses on the cycloisomerization of α,ω-dienes using a ruthenium-carbene catalyst in combination with trimethylsilyl vinyl ether, exploring its application in the synthesis of heterocyclic compounds, specifically 3-methylene-2,3-dihydroindoles and 3-methylene-2,3-dihydrobenzofurans. The ruthenium-carbene catalyst B, along with other catalysts A, C, and D, were used to promote the cycloisomerization reaction, which is a highly atom-economic method for constructing carbo- and heterocycles. Trimethylsilyl vinyl ether (2a) was employed as a reagent to facilitate the cycloisomerization process, leading to the formation of the desired heterocyclic compounds. The study also investigated the role of N-heterocyclic carbene (NHC) ligands in the ruthenium catalysts, highlighting their importance for efficient cycloisomerizations in terms of regio- and chemoselectivity. The purpose of these chemicals was to develop a novel synthesis methodology for exo-methylene heterocyclic compounds, which are potential key intermediates for pharmacologically active compounds, and to gain further insights into the chemistry of ruthenium-carbene complexes.