ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate

Base Information

• Chemical Name: ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate
• CAS No.: 122135-98-2
• Molecular Formula: C₁₄H₁₅F₃O₅S
• Molecular Weight: 352.331
• Mol file: 122135-98-2.mol

Synonyms:ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate

Chemical Property of ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate

There total 4 articles about ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate 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: 55.0%

trifluoromethylsulfonic anhydride (358-23-6) + ethyl 3-oxo-5-phenylpentanoate (17071-29-3) → ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate (122135-98-2) + ethyl (Z)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate (122135-86-8)

Guidance literature:

ethyl 3-oxo-5-phenylpentanoate; With tetramethyl ammoniumhydroxide; In hexane; water; at 5 - 10 ℃; for 0.0833333h;

trifluoromethylsulfonic anhydride; In hexane; water; at 5 - 15 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1021/ol8010002

Reference yield: 33.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + ethyl acetoacetate (141-97-9) → ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate (122135-98-2)

Guidance literature:

ethyl acetoacetate; PhCH₂-X; With n-butyllithium; sodium hydride; In tetrahydrofuran; at -78 ℃;

N,N-phenylbistrifluoromethane-sulfonimide; In tetrahydrofuran; at 0 ℃;

DOI:10.1055/s-2001-14908

Reference yield: 33.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + benzyl bromide (100-39-0) + ethyl acetoacetate (141-97-9) → ethyl (E)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate (122135-98-2)

Guidance literature:

ethyl acetoacetate; With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; at 0 ℃; for 0.166667h;

benzyl bromide; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

N,N-phenylbistrifluoromethane-sulfonimide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1016/j.bmc.2004.04.047

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

ethyl acetoacetate

benzyl bromide

trifluoromethylsulfonic anhydride

Downstream raw materials:

(2E,4E,6Z,8E)-7-Methyl-3-phenethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid ethyl ester

ethyl (2E,4E,6E,8E)-7-methyl-3-(2-phenyl)ethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate

5-phenyl-penta-2,3-dienoic acid ethyl ester