ethyl 4-<(E)-2-<3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>phenyl>ethenyl>benzoate

Base Information

Chemical Name:ethyl 4-<(E)-2-<3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>phenyl>ethenyl>benzoate
CAS No.:146998-39-2
Molecular Formula:C₃₃H₄₄O₃Si
Molecular Weight:516.796
Hs Code.:

Synonyms:ethyl 4-<(E)-2-<3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>phenyl>ethenyl>benzoate

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Chemical Property of ethyl 4-<(E)-2-<3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>phenyl>ethenyl>benzoate

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Technology Process of ethyl 4-<(E)-2-<3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>phenyl>ethenyl>benzoate

There total 5 articles about ethyl 4-<(E)-2-<3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>phenyl>ethenyl>benzoate 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: 51.0%

: 71441-08-2
ethyl 4-(diethoxyphosphorylmethyl)benzoate

: 107430-94-4
3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>benzenecarboxaldehyde

: 146998-39-2
ethyl 4-<(E)-2-<3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>phenyl>ethenyl>benzoate

Guidance literature:: With 15-crown-5; sodium hydride; In tetrahydrofuran; Ambient temperature;
DOI:10.1021/jm00026a006

Reference yield:

: 106-41-2
4-bromo-phenol

: 146998-39-2
ethyl 4-<(E)-2-<3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>phenyl>ethenyl>benzoate

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / conc. H₂SO₄ / CH₂Cl₂ / 8 h / Ambient temperature

2: 86 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / dimethylformamide / 4 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, -70 deg C, 45 min, 2.) THF, from -40 deg C to RT

4: 51 percent / NaH, 15-crown-5 / tetrahydrofuran / Ambient temperature

With dmap; n-butyllithium; 15-crown-5; sulfuric acid; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00026a006

Reference yield:

: 768-95-6
1-adamanthanol

: 146998-39-2
ethyl 4-<(E)-2-<3-(1-adamantyl)-4-<(tert-butyldimethylsilyl)oxy>phenyl>ethenyl>benzoate

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / conc. H₂SO₄ / CH₂Cl₂ / 8 h / Ambient temperature

2: 86 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / dimethylformamide / 4 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, -70 deg C, 45 min, 2.) THF, from -40 deg C to RT

4: 51 percent / NaH, 15-crown-5 / tetrahydrofuran / Ambient temperature

With dmap; n-butyllithium; 15-crown-5; sulfuric acid; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00026a006