(S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

Base Information

Chemical Name:(S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate
CAS No.:1239568-83-2
Molecular Formula:C₁₈H₂₇BO₄
Molecular Weight:318.221
Hs Code.:

Synonyms:(S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

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Technology Process of (S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

There total 5 articles about (S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate 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: 92.0%

: 945-93-7,13979-22-1,1504-72-9
ethyl (E)-3-phenylbut-2-enoate

: 73183-34-3
bis(pinacol)diborane

: 1239568-83-2
(S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

Guidance literature:: bis(pinacol)diborane; With 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; at 17 - 18 ℃; for 0.166667h; Inert atmosphere;

ethyl (E)-3-phenylbut-2-enoate; With methanol; tetradecane; In tetrahydrofuran; at 17 - 18 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Sealed tube;
DOI:10.1002/chem.201002361

Reference yield: 61.0%

: 945-93-7,1504-72-9,13979-22-1
ethyl (Z)-3-phenylbut-2-enoate

: 73183-34-3
bis(pinacol)diborane

: 1239568-83-2
(S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

Guidance literature:: With CuCl; NaOC(CH₃)3; (C₆H₅C₆H₄(NC₃H₂N)(C₆H₅)2C₆H₂(CH(CH₃)2)3)BF₄; In tetrahydrofuran; methanol; under N2; carboxylic ester, CuCl (5 mol.-%), NaOtBu (13 mol.-%), bis(pinacolato)diboron (1.1 equiv.), MeOH (1.2 equiv.), THF, and imidazolium salt (5 mol.-%) mixed at -30°C, mixt. stored for 18 h; 30% HCl and MeOH added, 89.5:10.5 er;
DOI:10.1021/ja104777u

Reference yield:

: 1504-72-9,13979-22-1,945-93-7
ethyl 3-phenylbut-2-enoate

: 73183-34-3
bis(pinacol)diborane

: 1239568-83-2
(S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

: 1239569-09-5
(R)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

Guidance literature:: With C₃₆H₃₁F₂N₂⁽¹⁺⁾*BF₄^(1-); copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; methanol; at 20 ℃; for 12h; Overall yield = 12 percent; Schlenk technique; Inert atmosphere;
DOI:10.1246/BCSJ.20200122