5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal

Base Information

Chemical Name:5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal
CAS No.:157406-33-2
Molecular Formula:C₂₃H₃₀O₄Si
Molecular Weight:398.574
Hs Code.:

Synonyms:5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal

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Chemical Property of 5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal

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Technology Process of 5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal

There total 5 articles about 5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal 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: 84.0%

: 157406-30-9
5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentyn-1-ol

: 157406-33-2
5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal

Guidance literature:: With pyridinium chlorochromate; In dichloromethane; Ambient temperature;
DOI:10.1021/jo961049j

Reference yield:

: 26260-02-6
2-iodobenzaldehyde

: 157406-33-2
5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, hexanes, -20 deg C, 30 min, 2.) THF, room temperature, overnight

2: 82 percent / Et₃N / CH₂Cl₂ / 7 h / Ambient temperature

3: 32 percent / Pd(PPh₃)2Cl₂, Et₃N, CuI / tetrahydrofuran / 48 h / Ambient temperature

4: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo961049j

Reference yield:

: 5159-41-1
2-iodobenzyl alcohol

: 157406-33-2
5-<2-(1-acetoxy-4-((tert-butyldimethylsilyl)oxy)-2-butynyl)phenyl>-4-pentynal

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / pyridinium chloroformate / CH₂Cl₂ / Ambient temperature

2: 1.) n-BuLi / 1.) THF, hexanes, -20 deg C, 30 min, 2.) THF, room temperature, overnight

3: 82 percent / Et₃N / CH₂Cl₂ / 7 h / Ambient temperature

4: 32 percent / Pd(PPh₃)2Cl₂, Et₃N, CuI / tetrahydrofuran / 48 h / Ambient temperature

5: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; pyridinium chloroformate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo961049j