(E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester
• CAS No.: 356793-34-5
• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.279
• Mol file: 356793-34-5.mol

Synonyms:(E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

Chemical Property of (E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

There total 7 articles about (E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl 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: 70.0%

bromoacetic acid methyl ester (96-32-2) + (R,E)-3-hydroxy-5-phenylpent-4-enenitrile (132203-22-6) → (E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester (356793-34-5)

Guidance literature:

(R,E)-3-hydroxy-5-phenylpent-4-enenitrile; With zinc; In tetrahydrofuran; at 50 ℃; for 0.166667h; ultrasound;

bromoacetic acid methyl ester; In benzene; at 50 ℃; for 5h; irradiation;

DOI:10.1055/s-2005-871953

Reference yield:

Toluene-4-sulfonic acid (E)-(S)-2-hydroxy-4-phenyl-but-3-enyl ester → (E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester (356793-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. ethanol / 24 h / 0 - 20 °C

2.1: Zn / tetrahydrofuran / 0.17 h / 50 °C / ultrasound

2.2: 70 percent / benzene / 5 h / 50 °C / irradiation

With zinc; In tetrahydrofuran; ethanol; 2.1: Blaise reaction;

DOI:10.1055/s-2005-871953

Reference yield:

benzyltriphenylphosphonium bromide (1449-46-3) → (E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester (356793-34-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / BuLi / tetrahydrofuran / 2 h / 0 - 20 °C

2.1: 96 percent / HCl / tetrahydrofuran / 10 h / 20 °C

3.1: 83 percent / pyridine / 12 h / -17 - 20 °C

4.1: aq. ethanol / 24 h / 0 - 20 °C

5.1: Zn / tetrahydrofuran / 0.17 h / 50 °C / ultrasound

5.2: 70 percent / benzene / 5 h / 50 °C / irradiation

With pyridine; hydrogenchloride; n-butyllithium; zinc; In tetrahydrofuran; ethanol; 1.1: Wittig olefination / 5.1: Blaise reaction;

DOI:10.1055/s-2005-871953

upstream raw materials:

bromoacetic acid methyl ester

(R,E)-3-hydroxy-5-phenylpent-4-enenitrile

(E)-(R)-3-Oxo-7-phenyl-5-trimethylsilanyloxy-hept-6-enoic acid methyl ester

(E)-3-phenylpropenal

Downstream raw materials:

Kavain

(R)-6-((E)-Styryl)-dihydro-pyran-2,4-dione

Refernces

• 1、 Wang, Fang-Dao,Yue, Jian-Min. "Total synthesis of (R)-(+)-kavain via (MeCN)2PdCl 2-catalyzed isomerization of a cis double bond and sonochemical Blaise reaction". . p. 2077 - 2079. Retrieved 2007/10/03.