3-(3-(3-(benzyloxy)-1-(2-nitrophenyl)propyl)-1-ethylcyclopent-2-en-1-yl)propan-1-ol

Base Information

• Chemical Name: 3-(3-(3-(benzyloxy)-1-(2-nitrophenyl)propyl)-1-ethylcyclopent-2-en-1-yl)propan-1-ol
• CAS No.: 1452824-00-8
• Molecular Formula: C₂₆H₃₃NO₄
• Molecular Weight: 423.552
• Mol file: 1452824-00-8.mol

Synonyms:3-(3-(3-(benzyloxy)-1-(2-nitrophenyl)propyl)-1-ethylcyclopent-2-en-1-yl)propan-1-ol

Chemical Property of 3-(3-(3-(benzyloxy)-1-(2-nitrophenyl)propyl)-1-ethylcyclopent-2-en-1-yl)propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3-(3-(benzyloxy)-1-(2-nitrophenyl)propyl)-1-ethylcyclopent-2-en-1-yl)propan-1-ol

There total 4 articles about 3-(3-(3-(benzyloxy)-1-(2-nitrophenyl)propyl)-1-ethylcyclopent-2-en-1-yl)propan-1-ol 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%

potassium 4-(benzyloxy)2-(2-nitrophenyl)butanoate (1452823-72-1) + 3-(3-((tert-butyldimethylsilyl)oxy)propyl)-3-ethylcyclopent-1-en-1-yl trifluoromethanesulfonate (1452823-74-3) → 3-(3-(3-(benzyloxy)-1-(2-nitrophenyl)propyl)-1-ethylcyclopent-2-en-1-yl)propan-1-ol (1452824-00-8)

Guidance literature:

potassium 4-(benzyloxy)2-(2-nitrophenyl)butanoate; 3-(3-((tert-butyldimethylsilyl)oxy)propyl)-3-ethylcyclopent-1-en-1-yl trifluoromethanesulfonate; With bis(η3-allyl-μ-chloropalladium(II)); XPhos; In diethylene glycol dimethyl ether; at 100 ℃; for 2h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ja509329x

Reference yield:

3-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)cyclopent-2-en-1-one (1452823-73-2) → 3-(3-(3-(benzyloxy)-1-(2-nitrophenyl)propyl)-1-ethylcyclopent-2-en-1-yl)propan-1-ol (1452824-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 1 h / -78 - -40 °C

1.2: 3 h / -40 °C

1.3: 24 h / 20 °C

2.1: bis(η3-allyl-μ-chloropalladium(II)); XPhos / diethylene glycol dimethyl ether / 2 h / 100 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

With copper(I) bromide dimethylsulfide complex; bis(η3-allyl-μ-chloropalladium(II)); XPhos; In tetrahydrofuran; diethylene glycol dimethyl ether;

DOI:10.1021/ja509329x

Reference yield:

3-ethoxycyclopent-2-en-1-one (22627-70-9) → 3-(3-(3-(benzyloxy)-1-(2-nitrophenyl)propyl)-1-ethylcyclopent-2-en-1-yl)propan-1-ol (1452824-00-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methylmagnesium chloride / tetrahydrofuran / 3 h / -78 - 20 °C

1.2: 2.33 h / 20 °C / Reflux

2.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 1 h / -78 - -40 °C

3.2: 3 h / -40 °C

3.3: 24 h / 20 °C

4.1: bis(η3-allyl-μ-chloropalladium(II)); XPhos / diethylene glycol dimethyl ether / 2 h / 100 °C / Inert atmosphere

4.2: 4 h / 20 °C / Inert atmosphere

With 1H-imidazole; copper(I) bromide dimethylsulfide complex; bis(η3-allyl-μ-chloropalladium(II)); methylmagnesium chloride; XPhos; In tetrahydrofuran; diethylene glycol dimethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/ja509329x

upstream raw materials:

3-(3'-hydroxypropyl)-2-cyclopenten-1-one

3-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)cyclopent-2-en-1-one

3-ethoxycyclopent-2-en-1-one

potassium 4-(benzyloxy)2-(2-nitrophenyl)butanoate