(-)-methyl 4-{[(1R)-1-methylprop-2-yn-1-yl]oxy}-3-[(2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}phenyl)ethynyl]benzoate

Base Information

Chemical Name:(-)-methyl 4-{[(1R)-1-methylprop-2-yn-1-yl]oxy}-3-[(2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}phenyl)ethynyl]benzoate
CAS No.:1393671-35-6
Molecular Formula:C₂₄H₂₀O₄
Molecular Weight:372.42
Hs Code.:

Synonyms:(-)-methyl 4-{[(1R)-1-methylprop-2-yn-1-yl]oxy}-3-[(2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}phenyl)ethynyl]benzoate

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Chemical Property of (-)-methyl 4-{[(1R)-1-methylprop-2-yn-1-yl]oxy}-3-[(2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}phenyl)ethynyl]benzoate

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Technology Process of (-)-methyl 4-{[(1R)-1-methylprop-2-yn-1-yl]oxy}-3-[(2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}phenyl)ethynyl]benzoate

There total 8 articles about (-)-methyl 4-{[(1R)-1-methylprop-2-yn-1-yl]oxy}-3-[(2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}phenyl)ethynyl]benzoate 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%

: 1393671-34-5
(-)-methyl 4-({(1R)-1-methyl-3-[tris(1-methylethyl)silyl]prop-2-yn-1-yl}oxy)-3-{[2-({(1R)-1-methyl-3-[tris(1-methylethyl)silyl]prop-2-yn-1-yl}oxy)phenyl]ethynyl}-benzoate

: 1393671-35-6
(-)-methyl 4-{[(1R)-1-methylprop-2-yn-1-yl]oxy}-3-[(2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}phenyl)ethynyl]benzoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1002/anie.201108307

Reference yield:

: 1393670-93-3
(+)-1-iodo-2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}benzene

: 1393671-35-6
(-)-methyl 4-{[(1R)-1-methylprop-2-yn-1-yl]oxy}-3-[(2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}phenyl)ethynyl]benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - 20 °C / Inert atmosphere

2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine / 2 h / 20 °C / Inert atmosphere

3.1: potassium carbonate / methanol / 2 h / 20 °C

4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine / 12 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; potassium carbonate; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; 2.1: Sonogashira coupling / 4.1: Sonogashira coupling;
DOI:10.1002/anie.201108307

Reference yield:

: 1393670-96-6
(+)-[(3R)-3-(2-ethynylphenoxy)but-1-yn-1-yl][tris(1-methylethyl)]silane

: 1393671-35-6
(-)-methyl 4-{[(1R)-1-methylprop-2-yn-1-yl]oxy}-3-[(2-{[(1R)-1-methylprop-2-yn-1-yl]oxy}phenyl)ethynyl]benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine / 12 h / 0 - 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; diisopropylamine; In tetrahydrofuran; 1: Sonogashira coupling;
DOI:10.1002/anie.201108307