6-[1-benzyl-5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde

Base Information

Chemical Name:6-[1-benzyl-5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde
CAS No.:606926-25-4
Molecular Formula:C₂₈H₄₀O₅Si
Molecular Weight:484.708
Hs Code.:

Synonyms:6-[1-benzyl-5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde

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Chemical Property of 6-[1-benzyl-5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde

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Technology Process of 6-[1-benzyl-5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde

There total 6 articles about 6-[1-benzyl-5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde 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: 85.0%

: 100-39-0
benzyl bromide

: 606926-21-0
6-[5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde

: 606926-25-4
6-[1-benzyl-5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde

Guidance literature:: With tetra(n-butyl)ammonium hydroxide; In dichloromethane; at 40 ℃;
DOI:10.1016/S0040-4020(03)01066-4

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 606926-25-4
6-[1-benzyl-5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: 96 percent / imidazole / dimethylformamide / 2 h / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 4.5 h / -40 - -30 °C

2.2: tetrahydrofuran; hexane / -78 - 20 °C

3.1: n-BuLi / tetrahydrofuran / 5.5 h / -20 - -10 °C

3.2: 75 percent / tetrahydrofuran / 20 °C

4.1: 95 percent / p-TsOH / acetone / 0.08 h / 20 °C

5.1: 83 percent / Hg(OAc)2 / acetonitrile; H₂O / 1 h / 20 °C

6.1: 85 percent / aq. tetra-n-butylammonium hydroxide / CH₂Cl₂ / 40 °C

With 1H-imidazole; n-butyllithium; mercury(II) diacetate; tetra(n-butyl)ammonium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1016/S0040-4020(03)01066-4

Reference yield:

: 606926-17-4
1-chloromethyl-2-dimethoxymethyl-3,5-dimethoxybenzene

: 606926-25-4
6-[1-benzyl-5-(tert-butyldimethylsilyloxy)-2-oxopentyl]-2,4-dimethoxy-3-methylbenzaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 4.5 h / -40 - -30 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: n-BuLi / tetrahydrofuran / 5.5 h / -20 - -10 °C

2.2: 75 percent / tetrahydrofuran / 20 °C

3.1: 95 percent / p-TsOH / acetone / 0.08 h / 20 °C

4.1: 83 percent / Hg(OAc)2 / acetonitrile; H₂O / 1 h / 20 °C

5.1: 85 percent / aq. tetra-n-butylammonium hydroxide / CH₂Cl₂ / 40 °C

With n-butyllithium; mercury(II) diacetate; tetra(n-butyl)ammonium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; water; acetone; acetonitrile;
DOI:10.1016/S0040-4020(03)01066-4