(E)-3-(1-Benzyl-1H-indol-3-yl)-2-nitro-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-(1-Benzyl-1H-indol-3-yl)-2-nitro-acrylic acid ethyl ester
• CAS No.: 176967-10-5
• Molecular Formula: C₂₀H₁₈N₂O₄
• Molecular Weight: 350.374
• Mol file: 176967-10-5.mol

Synonyms:(E)-3-(1-Benzyl-1H-indol-3-yl)-2-nitro-acrylic acid ethyl ester

Chemical Property of (E)-3-(1-Benzyl-1H-indol-3-yl)-2-nitro-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (E)-3-(1-Benzyl-1H-indol-3-yl)-2-nitro-acrylic acid ethyl ester

There total 1 articles about (E)-3-(1-Benzyl-1H-indol-3-yl)-2-nitro-acrylic acid ethyl 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%

1-Benzylindole-3-carboxaldehyde (10511-51-0) + ethyl nitroacetate sodium salt → (E)-3-(1-Benzyl-1H-indol-3-yl)-2-nitro-acrylic acid ethyl ester (176967-10-5)

Guidance literature:

With pyridine; titanium tetrachloride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.3987/com-95-7327

Reference yield: 87.0%

t-butyl malonate (541-16-2) + (E)-3-(1-Benzyl-1H-indol-3-yl)-2-nitro-acrylic acid ethyl ester (176967-10-5) → 3-(1-Benzyl-1H-indol-3-yl)-2-tert-butoxycarbonyl-4-nitro-pentanedioic acid 1-tert-butyl ester 5-ethyl ester (176967-11-6)

Guidance literature:

With potassium tert-butylate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.3987/com-95-7327

Reference yield:

(E)-3-(1-Benzyl-1H-indol-3-yl)-2-nitro-acrylic acid ethyl ester (176967-10-5) → [(3S,4S)-4-(1-Benzyl-1H-indol-3-yl)-2,6-dioxo-tetrahydro-pyran-3-yl]-carbamic acid allyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / t-BuOK / CH₂Cl₂; 2-methyl-propan-2-ol / Ambient temperature; 1.) 30 min, 2.) 1 h

2: 92 percent / H₂, Raney-Ni / ethanol; H₂O / 15 h / 760 Torr

3: 58 percent / pyridine; tetrahydrofuran / 1 h / Ambient temperature

4: 1.) 5percent aq. KOH, 2.) 4N HCl / 1.) dioxane, reflux, 3 h, 2.) reflux, 4 h

5: 88 percent / MsCl, Et₃N / tetrahydrofuran / 2 h / -30 °C

With hydrogenchloride; potassium hydroxide; potassium tert-butylate; hydrogen; nickel; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1080/00397919608004608

upstream raw materials:

1-Benzylindole-3-carboxaldehyde

Downstream raw materials:

3-(1-Benzyl-1H-indol-3-yl)-2-tert-butoxycarbonyl-4-nitro-pentanedioic acid 1-tert-butyl ester 5-ethyl ester

2-Amino-3-(1-benzyl-1H-indol-3-yl)-4-tert-butoxycarbonyl-pentanedioic acid 5-tert-butyl ester 1-ethyl ester