(R)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate

Base Information

• Chemical Name: (R)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate
• CAS No.: 1377848-15-1
• Molecular Formula: C₁₅H₁₃F₃O₄
• Molecular Weight: 314.261
• Mol file: 1377848-15-1.mol

Synonyms:

Chemical Property of (R)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate

There total 6 articles about (R)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate 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:

(E)-3-phenyl-2-butenoic acid (704-80-3) + ethyl-3,3,3-trifluoropyruvate (13081-18-0) → (R)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate (1377848-15-1) + (S)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate

Guidance literature:

(E)-3-phenyl-2-butenoic acid; With pivaloyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

ethyl-3,3,3-trifluoropyruvate; With (S)-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)(4-(pyrrolidin-1-yl)pyridin-3-yl)methanone; triethylamine; In dichloromethane; at 20 ℃; for 16h; Reagent/catalyst; Overall yield = 70 %; Optical yield = 11 %ee; enantioselective reaction; Molecular sieve; Inert atmosphere; Schlenk technique;

DOI:10.1002/cjoc.201600929

Reference yield:

acetophenone (98-86-2) → (R)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate (1377848-15-1) + (S)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydride / tetrahydrofuran; mineral oil / 12 h / 0 - 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

3: manganese(IV) oxide / chloroform / 20 - 60 °C

4: BF₄^(1-)*C₂₁H₂₂N₃O⁽¹⁺⁾; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; potassium carbonate; magnesium triflate; scandium tris(trifluoromethanesulfonate) / 24 h / 20 °C / Inert atmosphere

With manganese(IV) oxide; lithium aluminium tetrahydride; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; BF₄^(1-)*C₂₁H₂₂N₃O⁽¹⁺⁾; sodium hydride; potassium carbonate; magnesium triflate; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; chloroform; mineral oil;

DOI:10.1021/ja303618z

Reference yield:

methyl trans-3-methylcinnamate (3461-50-5) → (R)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate (1377848-15-1) + (S)-ethyl 6-oxo-4-phenyl-2-(trifluoromethyl)-3,6-dihydro-2H-pyran-2-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / 2 h / Reflux

2.1: triethylamine; pivaloyl chloride / dichloromethane / 0.5 h / 0 °C / Schlenk technique; Inert atmosphere

2.2: 16 h / 20 °C / Molecular sieve; Inert atmosphere; Schlenk technique

With pivaloyl chloride; triethylamine; sodium hydroxide; In dichloromethane;

DOI:10.1002/cjoc.201600929

upstream raw materials:

ethyl trifluoroacetate,

3-phenyl-2-butenal

ethyl 3-phenylbut-2-enoate

3-phenylbut-2-en-1-ol