tert-butyl 5-(bis(trimethylsilyl)methyl)-2-(2-(ethoxycarbonyl)allyl)benzoate

Base Information

Chemical Name:tert-butyl 5-(bis(trimethylsilyl)methyl)-2-(2-(ethoxycarbonyl)allyl)benzoate
CAS No.:1644191-37-6
Molecular Formula:C₂₄H₄₀O₄Si₂
Molecular Weight:448.75
Hs Code.:

Synonyms:tert-butyl 5-(bis(trimethylsilyl)methyl)-2-(2-(ethoxycarbonyl)allyl)benzoate

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Chemical Property of tert-butyl 5-(bis(trimethylsilyl)methyl)-2-(2-(ethoxycarbonyl)allyl)benzoate

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Technology Process of tert-butyl 5-(bis(trimethylsilyl)methyl)-2-(2-(ethoxycarbonyl)allyl)benzoate

There total 3 articles about tert-butyl 5-(bis(trimethylsilyl)methyl)-2-(2-(ethoxycarbonyl)allyl)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: 92.0%

: 1644191-30-9
tert-butyl 3-(bis(trimethylsilyl)methyl)benzoate

: 17435-72-2
ethyl 2-bromomethyl-2-propenoate

: 1644191-37-6
tert-butyl 5-(bis(trimethylsilyl)methyl)-2-(2-(ethoxycarbonyl)allyl)benzoate

Guidance literature:: tert-butyl 3-(bis(trimethylsilyl)methyl)benzoate; With bis(2,2,6,6-tetramethylpiperidinyl)magnesium lithium chloride; In tetrahydrofuran; at 25 ℃; for 2h; Schlenk technique; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; at -40 ℃; for 0.25h; Schlenk technique; Inert atmosphere;

ethyl 2-bromomethyl-2-propenoate; With copper(I) cyanide di(lithium chloride); In tetrahydrofuran; at -40 - 25 ℃; Schlenk technique; Inert atmosphere;
DOI:10.1002/chem.201402531

Reference yield:

: 69038-74-0
tert-butyl 3-bromobenzoate

: 1644191-37-6
tert-butyl 5-(bis(trimethylsilyl)methyl)-2-(2-(ethoxycarbonyl)allyl)benzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium chloride; magnesium; chloro-trimethyl-silane / tetrahydrofuran; ethylene dibromide / 0.5 h / 0 °C / Schlenk technique; Inert atmosphere

1.2: 2 h / 50 °C / Schlenk technique; Inert atmosphere

2.1: bis(2,2,6,6-tetramethylpiperidinyl)magnesium lithium chloride / tetrahydrofuran / 2 h / 25 °C / Schlenk technique; Inert atmosphere

2.2: 0.25 h / -40 °C / Schlenk technique; Inert atmosphere

2.3: -40 - 25 °C / Schlenk technique; Inert atmosphere

With chloro-trimethyl-silane; bis(2,2,6,6-tetramethylpiperidinyl)magnesium lithium chloride; magnesium; lithium chloride; In tetrahydrofuran; ethylene dibromide; 1.2: |Kumada Cross-Coupling;
DOI:10.1002/chem.201402531

Reference yield:

: 29955-12-2
bis(trimethylsilyl)methyl bromide

: 1644191-37-6
tert-butyl 5-(bis(trimethylsilyl)methyl)-2-(2-(ethoxycarbonyl)allyl)benzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium chloride; magnesium; chloro-trimethyl-silane / tetrahydrofuran; ethylene dibromide / 0.5 h / 0 °C / Schlenk technique; Inert atmosphere

1.2: 2 h / 50 °C / Schlenk technique; Inert atmosphere

2.1: bis(2,2,6,6-tetramethylpiperidinyl)magnesium lithium chloride / tetrahydrofuran / 2 h / 25 °C / Schlenk technique; Inert atmosphere

2.2: 0.25 h / -40 °C / Schlenk technique; Inert atmosphere

2.3: -40 - 25 °C / Schlenk technique; Inert atmosphere

With chloro-trimethyl-silane; bis(2,2,6,6-tetramethylpiperidinyl)magnesium lithium chloride; magnesium; lithium chloride; In tetrahydrofuran; ethylene dibromide; 1.2: |Kumada Cross-Coupling;
DOI:10.1002/chem.201402531