(-)-7-(2-hydroxy-5-methoxy-phenyl)-5-methyl-hept-6-ynoic acid methyl ester

Base Information

• Chemical Name: (-)-7-(2-hydroxy-5-methoxy-phenyl)-5-methyl-hept-6-ynoic acid methyl ester
• CAS No.: 333385-17-4
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332
• Mol file: 333385-17-4.mol

Synonyms:(-)-7-(2-hydroxy-5-methoxy-phenyl)-5-methyl-hept-6-ynoic acid methyl ester

Chemical Property of (-)-7-(2-hydroxy-5-methoxy-phenyl)-5-methyl-hept-6-ynoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-7-(2-hydroxy-5-methoxy-phenyl)-5-methyl-hept-6-ynoic acid methyl ester

There total 7 articles about (-)-7-(2-hydroxy-5-methoxy-phenyl)-5-methyl-hept-6-ynoic 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: 93.0%

2-iodo-4-methoxyl-phenol (312534-71-7) + (-)-methyl 5-methyl-6-heptynoate (333385-14-1) → (R)-5-(5-Methoxy-benzofuran-2-yl)-hexanoic acid methyl ester (333385-16-3) + (-)-7-(2-hydroxy-5-methoxy-phenyl)-5-methyl-hept-6-ynoic acid methyl ester (333385-17-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 25 ℃; for 24h;

DOI:10.1021/ja0021060

Reference yield:

N,N-diethyl-O-(4-methoxyphenyl)carbamate (85630-18-8) → (-)-7-(2-hydroxy-5-methoxy-phenyl)-5-methyl-hept-6-ynoic acid methyl ester (333385-17-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,N,N',N'-tetramethylethylenediamine; sec-BuLi / tetrahydrofuran / 1.5 h / -78 °C

1.2: I₂ / tetrahydrofuran / 0.5 h / -78 °C

2.1: 2N aq. NaOH / methanol / 96 h / Heating

3.1: 93 percent / NEt₃; CuI; bis(triphenylphosphine)Pd(II)Cl / dimethylformamide / 24 h / 25 °C

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja0021060

Reference yield:

cis-7-hydroxy-5-heptenoic acid,methyl ester (76871-77-7) → (-)-7-(2-hydroxy-5-methoxy-phenyl)-5-methyl-hept-6-ynoic acid methyl ester (333385-17-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Ti(i-PrO)4; (+)-diisopropyl-L-tartrate; tert-butyl hydroperoxide / CH₂Cl₂ / 3 h / -15 °C

2: 60 percent / CH₂Cl₂; hexane / 72 h / -78 °C

3: NaIO₄ / tetrahydrofuran; H₂O / 2 h / 25 °C

4: potassium t-butoxide / tetrahydrofuran / -50 °C

5: 93 percent / NEt₃; CuI; bis(triphenylphosphine)Pd(II)Cl / dimethylformamide / 24 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; copper(l) iodide; L-(+)-diisopropyl tartrate; potassium tert-butylate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja0021060

upstream raw materials:

2-iodo-4-methoxyl-phenol

(-)-methyl 5-methyl-6-heptynoate

N,N-diethyl-O-(4-methoxyphenyl)carbamate

cis-7-hydroxy-5-heptenoic acid,methyl ester