4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-bis-(methoxymethoxy)benzaldehyde

Base Information

Chemical Name:4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-bis-(methoxymethoxy)benzaldehyde
CAS No.:1178892-65-3
Molecular Formula:C₁₈H₃₀O₆Si
Molecular Weight:370.518
Hs Code.:

Synonyms:4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-bis-(methoxymethoxy)benzaldehyde

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Chemical Property of 4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-bis-(methoxymethoxy)benzaldehyde

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Technology Process of 4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-bis-(methoxymethoxy)benzaldehyde

There total 6 articles about 4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-bis-(methoxymethoxy)benzaldehyde 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: 99.0%

: 68-12-2,33513-42-7
N,N-dimethyl-formamide

: 444119-75-9
[4-bromo-3,5-bis(methoxymethoxy)phenyl]methoxy tert-butyldimethylsilane

: 1178892-65-3
4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-bis-(methoxymethoxy)benzaldehyde

Guidance literature:: [4-bromo-3,5-bis(methoxymethoxy)phenyl]methoxy tert-butyldimethylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.533333h; Inert atmosphere;

N,N-dimethyl-formamide; With calcium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; hexane;
DOI:10.1016/j.bmc.2009.04.071

Reference yield: 78.0%

: 68-12-2,33513-42-7
N,N-dimethyl-formamide

: 144337-52-0
3,5-bis(methoxymethoxy)-1-<<(tert-butyldimethylsilyl)oxy>methyl>benzene

: 1178892-65-3
4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-bis-(methoxymethoxy)benzaldehyde

Guidance literature:: 3,5-bis(methoxymethoxy)-1-<<(tert-butyldimethylsilyl)oxy>methyl>benzene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1.5h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at 0 - 20 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1021/ol301107m

Reference yield:

: 16534-12-6
3,5-dihydroxy-4-bromobenzoic acid

: 1178892-65-3
4-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-bis-(methoxymethoxy)benzaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 0 °C

2.1: sodium tetrahydroborate / tetrahydrofuran / 0.25 h / 65 °C

2.2: 2 h / Reflux

3.1: 1H-imidazole / dichloromethane / 14 h / 20 °C

4.1: diethyl ether / 0.33 h / -78 °C

4.2: -78 - 20 °C

With 1H-imidazole; sodium tetrahydroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/acs.joc.1c02046