1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)-2-(tert-butyldimethylsilyloxy)ethanol

Base Information

Chemical Name:1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)-2-(tert-butyldimethylsilyloxy)ethanol
CAS No.:258289-43-9
Molecular Formula:C₂₅H₃₆O₄Si
Molecular Weight:428.644
Hs Code.:

Synonyms:1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)-2-(tert-butyldimethylsilyloxy)ethanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)-2-(tert-butyldimethylsilyloxy)ethanol

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Technology Process of 1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)-2-(tert-butyldimethylsilyloxy)ethanol

There total 8 articles about 1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)-2-(tert-butyldimethylsilyloxy)ethanol 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: 92.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 258289-42-8
1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)ethane-1,2-diol

: 258289-43-9
1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)-2-(tert-butyldimethylsilyloxy)ethanol

Guidance literature:: With 1H-imidazole; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1248/cpb.47.1805

Reference yield:

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

: 258289-43-9
1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)-2-(tert-butyldimethylsilyloxy)ethanol

Guidance literature:: Multi-step reaction with 8 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

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; tetraethylammonium chloride; boron tribromide; potassium carbonate; magnesium; acetic acid; ethylene dibromide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 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

: 258289-43-9
1-(3-benzyloxy-2-ethenyl-5-methoxy-4-methylphenyl)-2-(tert-butyldimethylsilyloxy)ethanol

Guidance literature:: Multi-step reaction with 7 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

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; tetraethylammonium chloride; potassium carbonate; magnesium; acetic acid; ethylene dibromide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 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