5-[allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 5-[allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
• CAS No.: 285982-14-1
• Molecular Formula: C₃₇H₄₀NO₆P
• Molecular Weight: 625.701

Synonyms:5-[allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

Chemical Property of 5-[allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 5-[allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

There total 6 articles about 5-[allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 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: 78.0%

triphenylphosphine (603-35-0) + 5-(allyloxycarbonyl-hydroxy-methyl)-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (285982-11-8) → 5-[allyloxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (285982-14-1)

Guidance literature:

With N-chloro-succinimide; In dichloromethane; at 0 - 20 ℃; for 5h;

DOI:10.1246/cl.2000.492

Reference yield:

4-oxobutanoic acid methyl ester (13865-19-5) → 5-[allyloxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (285982-14-1)

Guidance literature:

Multi-step reaction with 5 steps

1: KOH / methanol / 2 h / 20 °C

2: DMAP / tetrahydrofuran / 1 h / 0 - 20 °C

3: DBU / acetonitrile / 3 h / 0 - 20 °C

4: 99 percent / ZnCl₂ / CH₂Cl₂ / 5 h / 20 °C

5: 78 percent / NCS / CH₂Cl₂ / 5 h / 0 - 20 °C

With dmap; potassium hydroxide; N-chloro-succinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1: Addition / 2: Acetylation / 3: cyclocondensation / 4: Addition / 5: Substitution;

DOI:10.1246/cl.2000.492

Reference yield:

methyl 4-hydroxybutanoate (925-57-5) → 5-[allyloxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (285982-14-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / PCC / CH₂Cl₂ / 1.5 h / 20 °C

2: KOH / methanol / 2 h / 20 °C

3: DMAP / tetrahydrofuran / 1 h / 0 - 20 °C

4: DBU / acetonitrile / 3 h / 0 - 20 °C

5: 99 percent / ZnCl₂ / CH₂Cl₂ / 5 h / 20 °C

6: 78 percent / NCS / CH₂Cl₂ / 5 h / 0 - 20 °C

With dmap; potassium hydroxide; N-chloro-succinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1: Oxidation / 2: Addition / 3: Acetylation / 4: cyclocondensation / 5: Addition / 6: Substitution;

DOI:10.1246/cl.2000.492

upstream raw materials:

triphenylphosphine

5-(allyloxycarbonyl-hydroxy-methyl)-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

4-oxobutanoic acid methyl ester

methyl 4-hydroxybutanoate

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