2H-Pyran-2-one, tetrahydro-5-methyl-6-phenyl-, (5R,6S)-rel-

Base Information

• Chemical Name: 2H-Pyran-2-one, tetrahydro-5-methyl-6-phenyl-, (5R,6S)-rel-
• CAS No.: 111120-85-5
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.242
• Mol file: 111120-85-5.mol

Synonyms:

Chemical Property of 2H-Pyran-2-one, tetrahydro-5-methyl-6-phenyl-, (5R,6S)-rel-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran-2-one, tetrahydro-5-methyl-6-phenyl-, (5R,6S)-rel-

There total 20 articles about 2H-Pyran-2-one, tetrahydro-5-methyl-6-phenyl-, (5R,6S)-rel- 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: 94.0%

4-methyl-5-oxo-5-phenylpentanal (88072-97-3) → (+/-)-(5R*,6S*)-6-Phenyl-5-methyltetrahydropyran-2-one (91496-12-7,111120-85-5,122358-15-0)

Guidance literature:

With samarium diiodide; 2-propanethiol; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/jo016058t

Reference yield:

5-p-methoxybenzyloxy-4-methyl-5-phenyl-pentanoic acid methyl ester → (+/-)-(5R*,6S*)-6-Phenyl-5-methyltetrahydropyran-2-one (91496-12-7,111120-85-5,122358-15-0) + (5RS,6SR)-6-phenyl-5-methyltetrahydropyran-2-one

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃; for 2h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(02)00968-7

Reference yield:

(E)-3-phenyl-2-methyl-2-propenol (1504-55-8,39924-63-5,55131-20-9) → (+/-)-(5R*,6S*)-6-Phenyl-5-methyltetrahydropyran-2-one (91496-12-7,111120-85-5,122358-15-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / 1.) VO(acac)2, 70percent aq. t-butylhydroperoxide / benzene / 1 h / 80 °C

2: 1.) oxalyl chloride, dmso, 2.) Et₃N / 1.) CH₂Cl₂, -50 deg C, 1 h, 2.) room temp., 15 min

3: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) 30 min

4: formic acid, Et₃N / Pd₂(dba)CHCl₃-n-Bu₃P / benzene / Ambient temperature; other solvents

5: H₂ / 5percent Pd/C / ethyl acetate / 10 h / Ambient temperature

6: 10percent aq. NaOH / diethyl ether / 8 h / Ambient temperature

7: p-toluenesulfonic acid / benzene / 2 h / Heating

With tert.-butylhydroperoxide; sodium hydroxide; formic acid; oxalyl dichloride; bis(acetylacetonate)oxovanadium; hydrogen; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; tributylphosphine; Pd₂(dba)(CHCl₃); In diethyl ether; ethyl acetate; benzene;

DOI:10.1021/ja00198a045

upstream raw materials:

(4R^*,5S^*)-5-Hydroxy-4-methyl-5-phenylpentanoic acid

4-methyl-5-oxo-5-phenylpentanal

2-Methyl-1-phenyl-4-pentyn-1-ol

2-methyl-1-phenylpentan-4-yn-1-one