(S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol

Base Information

• Chemical Name: (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol
• CAS No.: 1198785-20-4
• Molecular Formula: C₁₆H₁₈F₄O
• Molecular Weight: 302.312
• Mol file: 1198785-20-4.mol

Synonyms:(S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol

Chemical Property of (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol

There total 7 articles about (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-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: 83.0%

(R)-2-[2-(5-Fluoro-2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane + trimethylsilylacetylene (1066-54-2) → (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol (1198785-20-4)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 1h; Inert atmosphere;

(R)-2-[2-(5-Fluoro-2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane; In tetrahydrofuran; hexane; dimethyl sulfoxide; at 0 - 20 ℃; for 14h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; hexane; water; dimethyl sulfoxide; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/jlcr.3349

Reference yield: 65.0%

(R)-2-[2-(5-fluoro-2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane + lithium trimethylsilylacetylenide (54655-07-1) → (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol (1198785-20-4)

Guidance literature:

(R)-2-[2-(5-fluoro-2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane; lithium trimethylsilylacetylenide; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃; for 5h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1.08333h;

Reference yield:

1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methylpentan-2-one + trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane (129217-85-2) → (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol (1198785-20-4) + (R)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol

Guidance literature:

1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methylpentan-2-one; trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane; With (S)-1-isopropyl-pyrrolidine-2-carboxylic acid; water; diethylzinc; In tetrahydrofuran; toluene; at 20 ℃; for 1.66667h; Inert atmosphere;

With sodium methylate; In methanol; at 20 - 35 ℃; for 0.666667h; Overall yield = 71 %; Overall yield = 63.7 g;

DOI:10.1021/jo400080y

upstream raw materials:

lithium trimethylsilylacetylenide

trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane

trimethylsilylacetylene

(S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol