rac-2,4,5,6-Tetrahydro-4β*-hydroxy-2-oxo-6β*-methyl-6-benzofurancarboxylic acid methyl ester

Base Information

• Chemical Name: rac-2,4,5,6-Tetrahydro-4β*-hydroxy-2-oxo-6β*-methyl-6-benzofurancarboxylic acid methyl ester
• CAS No.: 84709-20-6
• Molecular Formula: C₁₁H₁₂O₅
• Molecular Weight: 224.213
• Mol file: 84709-20-6.mol

Synonyms:rac-2,4,5,6-Tetrahydro-4β*-hydroxy-2-oxo-6β*-methyl-6-benzofurancarboxylic acid methyl ester

Chemical Property of rac-2,4,5,6-Tetrahydro-4β*-hydroxy-2-oxo-6β*-methyl-6-benzofurancarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-2,4,5,6-Tetrahydro-4β*-hydroxy-2-oxo-6β*-methyl-6-benzofurancarboxylic acid methyl ester

There total 22 articles about rac-2,4,5,6-Tetrahydro-4β*-hydroxy-2-oxo-6β*-methyl-6-benzofurancarboxylic 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: 34.0%

3-Benzenesulfinyl-6-methyl-2-oxo-2,4,5,6-tetrahydro-benzofuran-6-carboxylic acid methyl ester (82891-33-6) → 2,4,5,6-tetrahydro-4α-hydroxy-6α-methoxycarbonyl-6β-methyl-1-benzofuran-2-one (81470-24-8,84709-20-6) + 2,4,5,6-tetrahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-1-benzofuran-2-one (81470-25-9,84709-20-6)

Guidance literature:

In pyridine; water; at 35 - 37 ℃; for 1.5h;

DOI:10.1016/S0040-4020(01)87730-9

Reference yield: 34.0%

3-Benzenesulfinyl-6-methyl-2-oxo-2,4,5,6-tetrahydro-benzofuran-6-carboxylic acid methyl ester (82891-33-6) → 2,4,5,6-tetrahydro-4α-hydroxy-6α-methoxycarbonyl-6β-methyl-1-benzofuran-2-one (81470-24-8,84709-20-6) + 2,4,5,6-tetrahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-1-benzofuran-2-one (81470-25-9,84709-20-6)

Guidance literature:

In pyridine; water; at 35 - 37 ℃; for 1.5h;

DOI:10.1016/S0040-4020(01)87730-9

Reference yield:

methyl 2-methyl-3-oxopropanoate (51673-64-4) → 2,4,5,6-tetrahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-1-benzofuran-2-one (81470-25-9,84709-20-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 52 percent / KF / dimethylsulfoxide; 1,2-dimethoxy-ethane / 2 h

2: 96 percent / SOCl₂ / pyridine / 1 h

3: m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

4: 27 percent / pyridine; H₂O / 1.5 h / 35 - 37 °C

5: 1.) triphenylphosphine, acetic acid, diethyl azodicarboxylate, 2.) 6M HCl / 1.) THF, RT, 15h, 2.) dioxane, 20h, 30 deg C

With hydrogenchloride; thionyl chloride; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; potassium fluoride; In pyridine; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)87730-9

upstream raw materials:

3-Benzenesulfinyl-6-methyl-2-oxo-2,4,5,6-tetrahydro-benzofuran-6-carboxylic acid methyl ester

methyl 2-methyl-3-oxopropanoate

2,4,5,6-tetrahydro-6-methoxycarbonyl-6-methyl-3-phenylthio-1-benzofuran-2-one

2,4,5,6,7,7a-hexahydro-7-hydroxy-6-methoxycarbonyl-6-methyl-3-phenylthio-1-benzofuran-2-one

Downstream raw materials:

2,4,5,6-tetrahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-1-benzofuran-2-one

Refernces

• 1、 Kido, Fusao,Noda, Yoshihiro,Yoshikoshi, Akira. "Total Synthesis of (+/-)-Paniculide A based on a Novel Vinylfuranone Annelation". . p. 1209 - 1210. Retrieved 2007/10/02.