(Ss,R)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

Base Information

Chemical Name:(Ss,R)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol
CAS No.:1260245-40-6
Molecular Formula:C₂₄H₁₉F₃O₂S
Molecular Weight:428.475
Hs Code.:

Synonyms:(Ss,R)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

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Chemical Property of (Ss,R)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

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Technology Process of (Ss,R)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

There total 4 articles about (Ss,R)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol 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: 79.0%

: 1260245-55-3
(S)-1-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)ethanone

: 536-74-3
phenylacetylene

: 1260245-40-6
(Ss,R)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

: (Ss,S)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

Guidance literature:: phenylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

With cerium(III) chloride; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(S)-1-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)ethanone; In tetrahydrofuran; hexane; at -78 ℃; for 3h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol102567h

Reference yield:

: 455-19-6
4-Trifluoromethylbenzaldehyde

: 1260245-40-6
(Ss,R)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

: (Ss,S)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

1.3: -78 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

3.3: 3 h / -78 °C / Inert atmosphere

With n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 2.1: Dess-Martin oxidation;
DOI:10.1021/ol102567h

Reference yield:

: 1517-82-4
(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

: 1260245-40-6
(Ss,R)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

: (Ss,S)-2-(4'-trifluoromethyl-2'-(p-tolylsulfinyl)phenyl)-4-phenylbut-3-yn-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

1.3: -78 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

3.3: 3 h / -78 °C / Inert atmosphere

With n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 2.1: Dess-Martin oxidation;
DOI:10.1021/ol102567h