2-(3-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile

Base Information

• Chemical Name: 2-(3-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile
• CAS No.: 79987-86-3
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• Mol file: 79987-86-3.mol

Synonyms:

Chemical Property of 2-(3-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(3-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile

There total 1 articles about 2-(3-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile 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:

3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide (33821-94-2) + 3-methoxyphenylacetonitrile (19924-43-7) → 2-(3-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile (79987-86-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1002/recl.19811000909

Reference yield:

2-(3-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile (79987-86-3) → 3-(3-hydroxyphenyl)-N-phenethylpiperidine (19725-24-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 25percent sulfuric acid, 8N chromic acid / acetone

2: KOH / ethanol; H₂O / 6 h / Heating

3: 74 percent / acetic anhydride / 3 h / Heating

4: 2.) acetic anhydride / 1.) benzene, 1 h, reflux; 2.) 5 h, reflux

5: 92 percent / boron tribromide / CH₂Cl₂ / 2 h / Ambient temperature

6: 85 percent / potassium carbonate / dimethylformamide

7: 76 percent / LiAlH₄ / tetrahydrofuran / Heating

8: 87 percent / H₂ / 10percent Pd-C / acetic acid

With potassium hydroxide; lithium aluminium tetrahydride; sulfuric acid; hydrogen; acetic anhydride; boron tribromide; chromic acid; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1002/recl.19811000909

Reference yield:

2-(3-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile (79987-86-3) → 1-propyl-3-(3-hydroxyphenyl)piperidine (75240-91-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 25percent sulfuric acid, 8N chromic acid / acetone

2: KOH / ethanol; H₂O / 6 h / Heating

3: 74 percent / acetic anhydride / 3 h / Heating

4: 2.) acetic anhydride / 1.) benzene, 1 h, reflux; 2.) 5 h, reflux

5: 93 percent / boron tribromide / CH₂Cl₂ / 2 h / Ambient temperature

6: 82 percent / potassium carbonate / dimethylformamide / 5 h

7: 91 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

8: 88 percent / H₂ / 10percent Pd-C / acetic acid / 4 h

With potassium hydroxide; lithium aluminium tetrahydride; sulfuric acid; hydrogen; acetic anhydride; boron tribromide; chromic acid; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1002/recl.19811000909

upstream raw materials:

3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide

3-methoxyphenylacetonitrile

Downstream raw materials:

4-cyano-4-(3-methoxyphenyl)butyric acid

2-(3-methoxyphenyl)glutaric acid

3-(3-hydroxyphenyl)-N-phenethylpiperidine

1-propyl-3-(3-hydroxyphenyl)piperidine

Refernces