(1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone

Base Information

• Chemical Name: (1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone
• CAS No.: 1378428-01-3
• Molecular Formula: C₂₁H₁₇F₃O₃S
• Molecular Weight: 406.425

Synonyms:(1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone

Chemical Property of (1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone

There total 3 articles about (1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone 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: 60.0%

furan (110-00-9) + (E,S)-4,4,4-trifluoro-1-[2-(p-tolylsulfinyl)phenyl]but-2-en-1-one (1378383-75-5) → (1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone (1378428-01-3) + C21H17F3O3S + C21H17F3O3S + C21H17F3O3S

Guidance literature:

With ytterbium(III) triflate; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tet.2012.03.112

Reference yield:

(S)-1-[2-(p-tolylsulfinyl)phenyl]ethanone → (1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone (1378428-01-3) + C21H17F3O3S + C21H17F3O3S + C21H17F3O3S

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; n-heptane / 0.33 h / 20 °C / Inert atmosphere

1.2: 3 h / 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C

3.1: ytterbium(III) triflate / acetonitrile / 20 °C

With boron trifluoride diethyl etherate; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; n-heptane; dichloromethane; acetonitrile; 3.1: Diels-Alder reaction;

DOI:10.1016/j.tet.2012.03.112

Reference yield:

C18H22O2SSi → (1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone (1378428-01-3) + C21H17F3O3S + C21H17F3O3S + C21H17F3O3S

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C

2: ytterbium(III) triflate / acetonitrile / 20 °C

With boron trifluoride diethyl etherate; ytterbium(III) triflate; In dichloromethane; acetonitrile; 2: Diels-Alder reaction;

DOI:10.1016/j.tet.2012.03.112

upstream raw materials:

furan

(E,S)-4,4,4-trifluoro-1-[2-(p-tolylsulfinyl)phenyl]but-2-en-1-one

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