(E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate

Base Information

• Chemical Name: (E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate
• CAS No.: 1465030-33-4
• Molecular Formula: C₁₉H₁₅NO₄
• Molecular Weight: 321.332
• Mol file: 1465030-33-4.mol

Synonyms:(E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate

Chemical Property of (E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate

There total 7 articles about (E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate 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: 79.0%

(E)-methyl 3-(4-((tert-butyldimethylsilyl)oxy)phenyl)-2-(1H-indol-2-yl)acrylate + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate (1465030-33-4)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; for 0.25h;

(E)-methyl 3-(4-((tert-butyldimethylsilyl)oxy)phenyl)-2-(1H-indol-2-yl)acrylate; In 1,2-dichloro-ethane; for 1h; Reflux;

DOI:10.24820/ark.5550190.p010.464

Reference yield: 76.0%

methyl 2-(3-formyl-1H-indol-2-yl)acetate (64951-03-7) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → (E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate (1465030-33-4)

Guidance literature:

With L-proline; In dimethyl sulfoxide; at 20 ℃; for 80h; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c3ob41573b

Reference yield:

2-Aminobenzyl alcohol (5344-90-1) → (E)-methyl α-(3-formyl-1H-indol-2-yl)-β-(4-benzyloxy-3-methoxyphenyl)acrylate (1465030-33-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetonitrile

2.1: dichloromethane / 3 h

3.1: potassium tert-butylate / toluene / 6 h / Reflux

4.1: dmap / tetrahydrofuran / 20 °C

5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -75 °C

5.2: -75 - 20 °C

5.3: 1 h / Reflux

6.1: trichlorophosphate / 0.25 h

6.2: 1 h / Reflux

With dmap; potassium tert-butylate; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;

DOI:10.24820/ark.5550190.p010.464

upstream raw materials:

methyl 2-(3-formyl-1H-indol-2-yl)acetate

4-hydroxy-benzaldehyde

N,N-dimethyl-formamide

2-Aminobenzyl alcohol

Downstream raw materials:

(E)-1-(tert-butoxycarbonyl)-2-(1-(4-((tert-butoxycarbonyl)oxy)phenyl)-3-methoxy-3-oxoprop-1-en-2-yl)-1H-indole-3-carboxylic acid

1-methoxycarbonyl-2-(4-hydroxyphenyl)-3-nitro-9H-carbazole

Refernces

• 1、 Biswas, Soumen,Jaiswal, Pradeep Kumar,Singh, Shivendra,Mobin, Shaikh M.,Samanta, Sampak. "L-Proline catalyzed stereoselective synthesis of (E)-methyl-α-indol- 2-yl-β-aryl/alkyl acrylates: Easy access to substituted carbazoles, γ-carbolines and prenostodione". supporting information. p. 7084 - 7087. Retrieved 2013/10/22.