3-phenyl-acrylic acid 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-2-oxo-propyl ester

Base Information

• Chemical Name: 3-phenyl-acrylic acid 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-2-oxo-propyl ester
• CAS No.: 854737-68-1
• Molecular Formula: C₂₅H₃₂O₅Si
• Molecular Weight: 440.612

Synonyms:3-phenyl-acrylic acid 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-2-oxo-propyl ester

Chemical Property of 3-phenyl-acrylic acid 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-2-oxo-propyl ester

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Technology Process of 3-phenyl-acrylic acid 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-2-oxo-propyl ester

There total 5 articles about 3-phenyl-acrylic acid 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-2-oxo-propyl ester 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: 70.0%

1-bromo-2-keto-3-(3-methoxy-4-t-butyldimethylsilyloxy)phenyl propane (854737-55-6) + (E)-3-phenylacrylic acid (140-10-3) → 3-phenyl-acrylic acid 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-2-oxo-propyl ester (854737-68-1)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In toluene; at 20 ℃;

DOI:10.1016/j.tet.2005.03.074

Reference yield:

1-bromo-2-hydroxy-3-(3-methoxy-4-t-butyldimethylsilyloxy)phenyl propane (854737-56-7) → 3-phenyl-acrylic acid 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-2-oxo-propyl ester (854737-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Dess-Martin reagent / CH₂Cl₂ / 15 h / 20 °C

2: 70 percent / aq. NaOH; NBu₄Br / toluene / 20 °C

With sodium hydroxide; tetrabutylammomium bromide; Dess-Martin periodane; In dichloromethane; toluene; 1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2005.03.074

Reference yield:

4-allylguaiacol (97-53-0) → 3-phenyl-acrylic acid 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-2-oxo-propyl ester (854737-68-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

2: 78 percent / NBS; H₂O / dimethylsulfoxide / 0 °C

3: 78 percent / Dess-Martin reagent / CH₂Cl₂ / 15 h / 20 °C

4: 70 percent / aq. NaOH; NBu₄Br / toluene / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; N-Bromosuccinimide; tetrabutylammomium bromide; water; Dess-Martin periodane; In dichloromethane; dimethyl sulfoxide; toluene; 3: Dess-Martin oxidation;

DOI:10.1016/j.tet.2005.03.074

upstream raw materials:

1-bromo-2-keto-3-(3-methoxy-4-t-butyldimethylsilyloxy)phenyl propane

(E)-3-phenylacrylic acid

1-bromo-2-hydroxy-3-(3-methoxy-4-t-butyldimethylsilyloxy)phenyl propane

4-allylguaiacol

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