(R)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline

Base Information

• Chemical Name: (R)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline
• CAS No.: 1299491-08-9
• Molecular Formula: C₁₆H₁₂F₃NO
• Molecular Weight: 291.273
• Mol file: 1299491-08-9.mol

Synonyms:

Chemical Property of (R)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline

There total 5 articles about (R)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline 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:

2-phenyl-5-[4-(trifluoromethyl)phenyl]-1,3-oxazole (778581-67-2) → (R)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline (1299491-08-9) + (S)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline

Guidance literature:

With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (R,R)-2,2″-bis[(S)-1-diphenylphosphinoethyl]-1,1″-biferrocene; hydrogen; In toluene; at 80 ℃; for 24h; under 38002.6 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1021/ja201543h

Reference yield:

2-azido-1-[4-(trifluoromethyl)phenyl]-1-ethanone (874813-04-4) → (R)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline (1299491-08-9) + (S)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; water / 21 h / 20 °C / Cooling with NaCl-ice

2: sodium hydrogencarbonate / water; ethyl acetate / 3.03 h / 0 - 20 °C

3: sulfuric acid / 0.33 h / 20 °C

4: [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (R,R)-2,2″-bis[(S)-1-diphenylphosphinoethyl]-1,1″-biferrocene; hydrogen / toluene / 24 h / 80 °C / 38002.6 Torr / Autoclave

With hydrogenchloride; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); sulfuric acid; (R,R)-2,2″-bis[(S)-1-diphenylphosphinoethyl]-1,1″-biferrocene; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; In methanol; water; ethyl acetate; toluene;

DOI:10.1021/ja201543h

Reference yield:

2-amino-1-[4-(trifluoromethyl)phenyl]-1-ethanone hydrogen chloride (339-58-2) → (R)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline (1299491-08-9) + (S)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydrogencarbonate / water; ethyl acetate / 3.03 h / 0 - 20 °C

2: sulfuric acid / 0.33 h / 20 °C

3: [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (R,R)-2,2″-bis[(S)-1-diphenylphosphinoethyl]-1,1″-biferrocene; hydrogen / toluene / 24 h / 80 °C / 38002.6 Torr / Autoclave

With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); sulfuric acid; (R,R)-2,2″-bis[(S)-1-diphenylphosphinoethyl]-1,1″-biferrocene; hydrogen; sodium hydrogencarbonate; In water; ethyl acetate; toluene;

DOI:10.1021/ja201543h

upstream raw materials:

2-azido-1-[4-(trifluoromethyl)phenyl]-1-ethanone

2-(N-benzoylamino)-1-[4-(trifluoromethyl)phenyl]-1-ethanone

2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone

2-amino-1-[4-(trifluoromethyl)phenyl]-1-ethanone hydrogen chloride

Downstream raw materials:

(R)-N-[2-hydroxy-2-{4-(trifluoromethyl)phenyl}ethyl]benzamide

C₂₅H₂₂F₃NO₄

C₂₅H₂₂F₃NO₄

Refernces