(E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one
• CAS No.: 1436872-10-4
• Molecular Formula: C₁₄H₁₁BrO₂
• Molecular Weight: 291.144
• Mol file: 1436872-10-4.mol

Synonyms:(E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one

Chemical Property of (E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one

There total 3 articles about (E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-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: 74.0%

2-phenyl-2-(prop-2-yn-1-yl)pent-4-ynoic acid → (E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one (1436872-10-4)

Guidance literature:

With N-Bromosuccinimide; dihydroquinidine; In hexane; chloroform; at -30 ℃; for 15.5h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201604003

Reference yield:

benzeneacetic acid methyl ester (101-41-7) → (E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one (1436872-10-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

1.2: 0 °C / Inert atmosphere; Schlenk technique

2.1: lithium hydroxide; water / tetrahydrofuran / 90 °C / Inert atmosphere; Schlenk technique

3.1: 18-crown-6 ether; potassium carbonate / chloroform; hexane / 1 h / 20 °C / Inert atmosphere; Schlenk technique

3.2: 0.25 h / -30 °C / Inert atmosphere; Schlenk technique

3.3: 15 h / -30 °C / Schlenk technique; Inert atmosphere

With 18-crown-6 ether; water; sodium hydride; potassium carbonate; lithium hydroxide; In tetrahydrofuran; hexane; chloroform; mineral oil;

DOI:10.1021/ja402910d

Reference yield:

2-phenyl-2-prop-2-ynylpent-4-ynoic acid methyl ester (22489-95-8) → (E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one (1436872-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hydroxide; water / tetrahydrofuran / 90 °C / Inert atmosphere; Schlenk technique

2.1: 18-crown-6 ether; potassium carbonate / chloroform; hexane / 1 h / 20 °C / Inert atmosphere; Schlenk technique

2.2: 0.25 h / -30 °C / Inert atmosphere; Schlenk technique

2.3: 15 h / -30 °C / Schlenk technique; Inert atmosphere

With 18-crown-6 ether; water; potassium carbonate; lithium hydroxide; In tetrahydrofuran; hexane; chloroform;

DOI:10.1021/ja402910d

upstream raw materials:

2-phenyl-2-prop-2-ynylpent-4-ynoic acid methyl ester

benzeneacetic acid methyl ester