(R,E)-methyl 5-(bromo(phenyl)methylene)-2-oxo-3-(3-phenylprop-2-ynyl)tetrahydrofuran-3-carboxylate

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Chemical Name:(R,E)-methyl 5-(bromo(phenyl)methylene)-2-oxo-3-(3-phenylprop-2-ynyl)tetrahydrofuran-3-carboxylate
CAS No.:1436871-97-4
Molecular Formula:C₂₂H₁₇BrO₄
Molecular Weight:425.279
Hs Code.:

Synonyms:(R,E)-methyl 5-(bromo(phenyl)methylene)-2-oxo-3-(3-phenylprop-2-ynyl)tetrahydrofuran-3-carboxylate

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Chemical Property of (R,E)-methyl 5-(bromo(phenyl)methylene)-2-oxo-3-(3-phenylprop-2-ynyl)tetrahydrofuran-3-carboxylate

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Technology Process of (R,E)-methyl 5-(bromo(phenyl)methylene)-2-oxo-3-(3-phenylprop-2-ynyl)tetrahydrofuran-3-carboxylate

There total 3 articles about (R,E)-methyl 5-(bromo(phenyl)methylene)-2-oxo-3-(3-phenylprop-2-ynyl)tetrahydrofuran-3-carboxylate 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: 83.0%

: 1374404-41-7
2-(methoxycarbonyl)-5-phenyl-2-(3-phenylprop-2-ynyl)pent-4-ynoic acid

: 1436871-97-4
(R,E)-methyl 5-(bromo(phenyl)methylene)-2-oxo-3-(3-phenylprop-2-ynyl)tetrahydrofuran-3-carboxylate

Guidance literature:: 2-(methoxycarbonyl)-5-phenyl-2-(3-phenylprop-2-ynyl)pent-4-ynoic acid; With Hydroquinone 1,4-phthalazinediyl diether; In hexane; chloroform; at -30 ℃; for 0.25h; Inert atmosphere; Schlenk technique;

With N-Bromosuccinimide; In hexane; chloroform; at -30 ℃; for 15h; enantioselective reaction; Inert atmosphere; Schlenk technique;
DOI:10.1021/ja402910d

Reference yield:

: 2,2-bis-(3-phenyl-prop-2-ynyl)-malonic acid dimethyl ester

: 1436871-97-4
(R,E)-methyl 5-(bromo(phenyl)methylene)-2-oxo-3-(3-phenylprop-2-ynyl)tetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hydroxide; methanol / Inert atmosphere; Schlenk technique

2.1: Hydroquinone 1,4-phthalazinediyl diether / chloroform; hexane / 0.25 h / -30 °C / Inert atmosphere; Schlenk technique

2.2: 15 h / -30 °C / Inert atmosphere; Schlenk technique

With methanol; Hydroquinone 1,4-phthalazinediyl diether; potassium hydroxide; In hexane; chloroform;
DOI:10.1021/ja402910d

Reference yield:

: 63104-44-9
dimethyl 2,2-di(prop-2-ynyl)malonate

: 1436871-97-4
(R,E)-methyl 5-(bromo(phenyl)methylene)-2-oxo-3-(3-phenylprop-2-ynyl)tetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere; Schlenk technique

2.1: potassium hydroxide; methanol / Inert atmosphere; Schlenk technique

3.1: Hydroquinone 1,4-phthalazinediyl diether / chloroform; hexane / 0.25 h / -30 °C / Inert atmosphere; Schlenk technique

3.2: 15 h / -30 °C / Inert atmosphere; Schlenk technique

With methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; Hydroquinone 1,4-phthalazinediyl diether; triethylamine; potassium hydroxide; In tetrahydrofuran; hexane; chloroform; 1.1: |Sonogashira Cross-Coupling;
DOI:10.1021/ja402910d