4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic acid tert-butyl ester

Base Information

• Chemical Name: 4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic acid tert-butyl ester
• CAS No.: 130351-29-0
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37
• Mol file: 130351-29-0.mol

Synonyms:4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic acid tert-butyl ester

Chemical Property of 4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic acid tert-butyl ester

There total 1 articles about 4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic 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:

ethyl crotonate (10544-63-5) + 4-(tert-butoxycarbonyl)benzaldehyde (65874-27-3) → 4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic acid tert-butyl ester (130351-29-0)

Guidance literature:

With potassium tert-butylate; In diethyl ether; tert-butyl alcohol; at 12 ℃; for 2h;

DOI:10.1021/jm00106a012

Reference yield:

4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic acid tert-butyl ester (130351-29-0) → 4-<2-(2,4-diamino-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoic acid (134373-15-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) H₂, 2.) 4-(N,N-dimethylamino)pyridine (DMAP), dicyclohexylcarbodiimide (DCC) / 1.) 5percent Pd/C / 1.) AcOEt, 4 at, 3 h, 2.) EtOH-CH₂Cl₂, 20 deg C, 18 h

2: 1.) LDA, 2.) I₂ / 1.) hexane, THF, -78 deg C, 10 min, 2.) a) -78 deg C, 20 min, b) from -78 deg C to 0 deg C, 30 min

3: 1.) NaH / 1.) Me₂SO, RT, 5 min, 2.) 20 deg C, 1 h

4: 89 percent / t-BuOK / 2-methyl-propan-2-ol / 4 h / Heating

5: 45 percent / BH₃-THF / 5 h / 0 °C

6: CF₃COOH / 2 h

With dmap; borane-THF; potassium tert-butylate; hydrogen; iodine; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tert-butyl alcohol;

DOI:10.1021/jm00106a012

Reference yield:

4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic acid tert-butyl ester (130351-29-0) → tert-butyl 4-<3-(2,4-diamino-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoate (125991-49-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) H₂, 2.) 4-(N,N-dimethylamino)pyridine (DMAP), dicyclohexylcarbodiimide (DCC) / 1.) 5percent Pd/C / 1.) AcOEt, 4 at, 3 h, 2.) EtOH-CH₂Cl₂, 20 deg C, 18 h

2: 1.) LDA, 2.) I₂ / 1.) hexane, THF, -78 deg C, 10 min, 2.) a) -78 deg C, 20 min, b) from -78 deg C to 0 deg C, 30 min

3: 1.) NaH / 1.) Me₂SO, RT, 5 min, 2.) 20 deg C, 1 h

4: 89 percent / t-BuOK / 2-methyl-propan-2-ol / 4 h / Heating

5: 45 percent / BH₃-THF / 5 h / 0 °C

With dmap; borane-THF; potassium tert-butylate; hydrogen; iodine; sodium hydride; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; In tert-butyl alcohol;

DOI:10.1021/jm00106a012

upstream raw materials:

ethyl crotonate

4-(tert-butoxycarbonyl)benzaldehyde

Downstream raw materials:

ethyl 5-<4-(tert-butoxycarbonyl)phenyl>pentanoate

ethyl 5-<4-(tert-butoxycarbonyl)phenyl>-2-iodopentanoate

ethyl 5-<4-(tert-butoxycarbonyl)phenyl>-2-(dicyanomethyl)pentanoate

4-<2-(2,4-diamino-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoic acid