5-(4-methoxy-3-methyl-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-pentanenitrile

Base Information

• Chemical Name: 5-(4-methoxy-3-methyl-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-pentanenitrile
• CAS No.: 288311-06-8
• Molecular Formula: C₃₁H₂₈NO₂P
• Molecular Weight: 477.543

Synonyms:5-(4-methoxy-3-methyl-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-pentanenitrile

Chemical Property of 5-(4-methoxy-3-methyl-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-pentanenitrile

Chemical Property:

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Technology Process of 5-(4-methoxy-3-methyl-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-pentanenitrile

There total 4 articles about 5-(4-methoxy-3-methyl-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-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-methyl-4-anisaldehyde (32723-67-4) → 5-(4-methoxy-3-methyl-phenyl)-3-oxo-2-(triphenyl-λ5-phosphanylidene)-pentanenitrile (288311-06-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / toluene / 48 h / Heating

2: 98 percent / H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

3: 98 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 4.5 h / 0 °C

4: oxalyl chloride / CH₂Cl₂ / 3 h / 20 °C

5: 711 mg / N,O-bis(trimethylsilyl)acetamide / CH₂Cl₂ / 5 h / 20 °C

With lithium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; 1: Addition / 2: Hydrogenation / 3: Hydrolysis / 4: Substitution / 5: Acylation;

DOI:10.1021/jo000458j

Reference yield:

ethyl (2E)-3-(4-methoxy-3-methylphenyl)acrylate (178676-97-6) → 5-(4-methoxy-3-methyl-phenyl)-3-oxo-2-(triphenyl-λ5-phosphanylidene)-pentanenitrile (288311-06-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

2: 98 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 4.5 h / 0 °C

3: oxalyl chloride / CH₂Cl₂ / 3 h / 20 °C

4: 711 mg / N,O-bis(trimethylsilyl)acetamide / CH₂Cl₂ / 5 h / 20 °C

With lithium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 1: Hydrogenation / 2: Hydrolysis / 3: Substitution / 4: Acylation;

DOI:10.1021/jo000458j

Reference yield:

3-(4-Methoxy-3-methyl-phenyl)-propionyl chloride (344308-94-7) + cyanomethylene triphenylphosphorane (16640-68-9) → 5-(4-methoxy-3-methyl-phenyl)-3-oxo-2-(triphenyl-λ5-phosphanylidene)-pentanenitrile (288311-06-8)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo000458j

upstream raw materials:

3-(4-Methoxy-3-methyl-phenyl)-propionyl chloride

cyanomethylene triphenylphosphorane

ethyl 3-(4-methoxy-3-methylphenyl)propinoate

3-methyl-4-anisaldehyde

Downstream raw materials:

methyl 4-(4-methoxy-3-methyl-phenyl)-2-oxo-butyrate

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