(Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

Base Information

Chemical Name:(Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate
CAS No.:1394236-77-1
Molecular Formula:C₂₁H₃₃ClO₃Si
Molecular Weight:397.03
Hs Code.:

Synonyms:(Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

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Chemical Property of (Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

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Technology Process of (Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

There total 5 articles about (Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate 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: 96.0%

: (5R,2Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-2-enoate

: 1394236-77-1
(Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

: 1394236-81-7
(Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

Guidance literature:: With ethylmagnesium bromide; copper(l) cyanide; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 1.16667h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol301988d

Reference yield:

: (3R)-methyl 2,2-dichloro-3-hydroxy-3-phenylpropionate

: 1394236-77-1
(Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

: 1394236-81-7
(Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-dimethylpyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C / Inert atmosphere

3: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 12.5 h / 0 - 20 °C / Inert atmosphere

4: copper(l) cyanide; ethylmagnesium bromide / tetrahydrofuran; diethyl ether / 1.17 h / -78 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; ethylmagnesium bromide; copper(l) cyanide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 3: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol301988d

Reference yield:

: C₁₅H₂₂Cl₂O₂Si

: 1394236-77-1
(Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

: 1394236-81-7
(Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-ethyl-5-phenylpent-3-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 12.5 h / 0 - 20 °C / Inert atmosphere

2: copper(l) cyanide; ethylmagnesium bromide / tetrahydrofuran; diethyl ether / 1.17 h / -78 - 20 °C / Inert atmosphere

With ethylmagnesium bromide; copper(l) cyanide; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; acetonitrile; 1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol301988d