1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}naphthalene

Base Information

Chemical Name:1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}naphthalene
CAS No.:860639-64-1
Molecular Formula:C₃₈H₃₀O
Molecular Weight:502.656
Hs Code.:

Synonyms:1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}naphthalene

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Chemical Property of 1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}naphthalene

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Technology Process of 1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}naphthalene

There total 6 articles about 1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}naphthalene 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: 35.0%

: 865448-83-5
triisopropyl(4-{1-{[2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}-1-naphthyl]ethynyl}-2-naphthyl}but-1-yn-1-yl)silane

: 860639-64-1
1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}naphthalene

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1135/cccc20042193

Reference yield:

: 624-31-7
4-tolyl iodide

: 860639-64-1
1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}naphthalene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 83 percent / CuI; (i-Pr)2NH / [PdCl₂(CH₃CN)2] / toluene / 3 h / 20 °C

2.1: BuLi / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C

2.2: 66 percent / tetrahydrofuran; dimethylsulfoxide / 16 h / 40 °C

3.1: 81 percent / CuI; (i-Pr)2NH / [Pd(PPh₃)4] / 2 h / 80 °C

4.1: 81 percent / NaOMe / methanol; tetrahydrofuran / 1 h / 20 °C

5.1: 58 percent / CuI; (i-Pr)2NH / [Pd(PPh₃)4] / 1 h / 20 °C

6.1: 35 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With copper(l) iodide; n-butyllithium; tetrabutyl ammonium fluoride; sodium methylate; diisopropylamine; dichloro bis(acetonitrile) palladium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dimethyl sulfoxide; toluene; 1.1: Sonogashira coupling / 3.1: Sonogashira coupling / 5.1: Sonogashira coupling;
DOI:10.1135/cccc20042193

Reference yield:

: 220983-57-3
(–)-(2S)-4-(4-methylphenyl)but-3-yn-2-ol

: 860639-64-1
1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methyl-3-p-tolylprop-2-yn-1-yl)oxy]methyl}naphthalene

Guidance literature:: Multi-step reaction with 5 steps

1.1: BuLi / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C

1.2: 66 percent / tetrahydrofuran; dimethylsulfoxide / 16 h / 40 °C

2.1: 81 percent / CuI; (i-Pr)2NH / [Pd(PPh₃)4] / 2 h / 80 °C

3.1: 81 percent / NaOMe / methanol; tetrahydrofuran / 1 h / 20 °C

4.1: 58 percent / CuI; (i-Pr)2NH / [Pd(PPh₃)4] / 1 h / 20 °C

5.1: 35 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With copper(l) iodide; n-butyllithium; tetrabutyl ammonium fluoride; sodium methylate; diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dimethyl sulfoxide; 2.1: Sonogashira coupling / 4.1: Sonogashira coupling;
DOI:10.1135/cccc20042193