(Z)-ethyl 2-(acetoxy(phenyl)methyl)-4-(tert-butyldimethylsilyloxy)but-2-enoate

Base Information

Chemical Name:(Z)-ethyl 2-(acetoxy(phenyl)methyl)-4-(tert-butyldimethylsilyloxy)but-2-enoate
CAS No.:1334334-73-4
Molecular Formula:C₂₁H₃₂O₅Si
Molecular Weight:392.568
Hs Code.:

Synonyms:(Z)-ethyl 2-(acetoxy(phenyl)methyl)-4-(tert-butyldimethylsilyloxy)but-2-enoate

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Chemical Property of (Z)-ethyl 2-(acetoxy(phenyl)methyl)-4-(tert-butyldimethylsilyloxy)but-2-enoate

Chemical Property:

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Technology Process of (Z)-ethyl 2-(acetoxy(phenyl)methyl)-4-(tert-butyldimethylsilyloxy)but-2-enoate

There total 4 articles about (Z)-ethyl 2-(acetoxy(phenyl)methyl)-4-(tert-butyldimethylsilyloxy)but-2-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: 90.0%

: 1334334-67-6
(Z)-ethyl 4-(tert-butyldimethylsilyloxy)-2-(hydroxy(phenyl)methyl)but-2-enoate

: 75-36-5
acetyl chloride

: 1334334-73-4
(Z)-ethyl 2-(acetoxy(phenyl)methyl)-4-(tert-butyldimethylsilyloxy)but-2-enoate

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1016/j.tetlet.2011.06.103

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1334334-73-4
(Z)-ethyl 2-(acetoxy(phenyl)methyl)-4-(tert-butyldimethylsilyloxy)but-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h

2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C

2.2: 12 h / -78 °C

3.1: diisobutylaluminium hydride; 4-methylmorpholine N-oxide / tetrahydrofuran / 2 h / 0 °C

3.2: 0 °C

4.1: pyridine / dichloromethane / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2011.06.103

Reference yield:

: 76782-82-6
tert-Butyldimethyl(prop-2-ynyloxy)silane

: 1334334-73-4
(Z)-ethyl 2-(acetoxy(phenyl)methyl)-4-(tert-butyldimethylsilyloxy)but-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C

1.2: 12 h / -78 °C

2.1: diisobutylaluminium hydride; 4-methylmorpholine N-oxide / tetrahydrofuran / 2 h / 0 °C

2.2: 0 °C

3.1: pyridine / dichloromethane / 2 h / 0 - 20 °C

With pyridine; n-butyllithium; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2011.06.103