ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate

Base Information

Chemical Name:ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate
CAS No.:1403338-24-8
Molecular Formula:C₃₃H₄₀FNO₄Si
Molecular Weight:561.769
Hs Code.:

Synonyms:ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate

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Chemical Property of ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate

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Technology Process of ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate

There total 4 articles about ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate 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:

: 148901-68-2,121660-63-7
(E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-propenal

: 1403338-24-8
ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -35 - -15 °C

1.2: 1 h / -80 - -75 °C

2.1: sodium hydroxide; water / tetrahydrofuran / 24 h / 20 - 30 °C

2.2: pH 1.5 - 2

2.3: 20 °C

3.1: hydrogenchloride; water / dichloromethane / 0 - 30 °C / pH 2 - 2.5

4.1: potassium iodide / N,N-dimethyl-formamide / 0.75 h / 25 - 65 °C / Inert atmosphere

4.2: 0.5 h / 60 - 65 °C

4.3: 0.5 h / 60 - 65 °C

5.1: dichloromethane / 3.25 h / 15 - 20 °C

6.1: zinc(II) oxide / toluene / 2 h / 25 - 30 °C / Inert atmosphere

6.2: 12 h

With hydrogenchloride; water; potassium iodide; zinc(II) oxide; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

: 1403338-21-5
(3S,4E)-5-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3-hydroxypentenoic acid (R)-α-methylbenzylamine salt

: 1403338-24-8
ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: hydrogenchloride; water / dichloromethane / 0 - 30 °C / pH 2 - 2.5

2.1: potassium iodide / N,N-dimethyl-formamide / 0.75 h / 25 - 65 °C / Inert atmosphere

2.2: 0.5 h / 60 - 65 °C

2.3: 0.5 h / 60 - 65 °C

3.1: dichloromethane / 3.25 h / 15 - 20 °C

4.1: zinc(II) oxide / toluene / 2 h / 25 - 30 °C / Inert atmosphere

4.2: 12 h

With hydrogenchloride; water; potassium iodide; zinc(II) oxide; In dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

: 1403338-20-4
(1S)-2-hydroxy-1,2,2-triphenylethyl (4E)-5-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3-hydroxy-4-pentenoate

: 1403338-24-8
ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydroxide; water / tetrahydrofuran / 24 h / 20 - 30 °C

1.2: pH 1.5 - 2

1.3: 20 °C

2.1: hydrogenchloride; water / dichloromethane / 0 - 30 °C / pH 2 - 2.5

3.1: potassium iodide / N,N-dimethyl-formamide / 0.75 h / 25 - 65 °C / Inert atmosphere

3.2: 0.5 h / 60 - 65 °C

3.3: 0.5 h / 60 - 65 °C

4.1: dichloromethane / 3.25 h / 15 - 20 °C

5.1: zinc(II) oxide / toluene / 2 h / 25 - 30 °C / Inert atmosphere

5.2: 12 h

With hydrogenchloride; water; potassium iodide; zinc(II) oxide; sodium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;