2-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)-1-(hydroxyimino)ethyl]-3-ethenyl-6-methoxytoluene

Base Information

Chemical Name:2-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)-1-(hydroxyimino)ethyl]-3-ethenyl-6-methoxytoluene
CAS No.:258289-45-1
Molecular Formula:C₂₅H₃₅NO₄Si
Molecular Weight:441.643
Hs Code.:

Synonyms:2-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)-1-(hydroxyimino)ethyl]-3-ethenyl-6-methoxytoluene

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Chemical Property of 2-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)-1-(hydroxyimino)ethyl]-3-ethenyl-6-methoxytoluene

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Technology Process of 2-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)-1-(hydroxyimino)ethyl]-3-ethenyl-6-methoxytoluene

There total 7 articles about 2-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)-1-(hydroxyimino)ethyl]-3-ethenyl-6-methoxytoluene 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: 57.0%

: 258289-44-0
2-benzyloxy-4-[α-(tert-butyldimethylsilyloxy)acetyl]-3-ethenyl-6-methoxytoluene

: 258289-45-1
2-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)-1-(hydroxyimino)ethyl]-3-ethenyl-6-methoxytoluene

Guidance literature:: With hydroxylamine hydrochloride; sodium acetate; In ethanol; at 85 ℃; for 1h;
DOI:10.1016/j.tet.2004.02.010

Reference yield:

: 7149-92-0
2,4-dimethoxy-3-methylbenzaldehyde

: 258289-45-1
2-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)-1-(hydroxyimino)ethyl]-3-ethenyl-6-methoxytoluene

Guidance literature:: Multi-step reaction with 10 steps

1.1: 83 percent / BBr₃ / CH₂Cl₂ / -78 - 20 °C

2.1: 99 percent / K₂CO₃ / dimethylformamide / 4 h / 60 °C

3.1: 88 percent / mCPBA / CH₂Cl₂ / 1 h / 60 °C

4.1: 53 percent / AcOH / 3 h / 110 °C

5.1: 81 percent / pyridine / CH₂Cl₂ / 1 h / cooling

6.1: 90 percent / Et₄NCl; PdCl₂(PPh₃)2 / dimethylformamide / 1.5 h / 110 °C

7.1: Mg; 1,2-dibromoethane / tetrahydrofuran

7.2: tetrahydrofuran / 2 h / 20 °C

7.3: 87 percent / H₂O₂; KHCO₃; KF / tetrahydrofuran; methanol / 3 h / 20 °C

8.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

9.1: 85 percent / pyridinium chlorochromate; celite / CH₂Cl₂ / 10 h / 20 °C

10.1: 57 percent / NH₂OH*HCl; AcONa / ethanol / 1 h / 85 °C

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; Celite; hydroxylamine hydrochloride; tetraethylammonium chloride; sodium acetate; boron tribromide; potassium carbonate; magnesium; acetic acid; ethylene dibromide; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Baeyer-Villiger reaction / 4.1: Duff reaction / 7.2: Grignard reaction;
DOI:10.1016/j.tet.2004.02.010

Reference yield:

: 54700-36-6
2-hydroxy-4-methoxy-3-methylbenzaldehyde

: 258289-45-1
2-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)-1-(hydroxyimino)ethyl]-3-ethenyl-6-methoxytoluene

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / K₂CO₃ / dimethylformamide / 4 h / 60 °C

2.1: 88 percent / mCPBA / CH₂Cl₂ / 1 h / 60 °C

3.1: 53 percent / AcOH / 3 h / 110 °C

4.1: 81 percent / pyridine / CH₂Cl₂ / 1 h / cooling

5.1: 90 percent / Et₄NCl; PdCl₂(PPh₃)2 / dimethylformamide / 1.5 h / 110 °C

6.1: Mg; 1,2-dibromoethane / tetrahydrofuran

6.2: tetrahydrofuran / 2 h / 20 °C

6.3: 87 percent / H₂O₂; KHCO₃; KF / tetrahydrofuran; methanol / 3 h / 20 °C

7.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

8.1: 85 percent / pyridinium chlorochromate; celite / CH₂Cl₂ / 10 h / 20 °C

9.1: 57 percent / NH₂OH*HCl; AcONa / ethanol / 1 h / 85 °C

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; Celite; hydroxylamine hydrochloride; tetraethylammonium chloride; sodium acetate; potassium carbonate; magnesium; acetic acid; ethylene dibromide; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Baeyer-Villiger reaction / 3.1: Duff reaction / 6.2: Grignard reaction;
DOI:10.1016/j.tet.2004.02.010