ethylene glycol phenyl(trimethylsilyl)methaneboronate

Base Information

Chemical Name:ethylene glycol phenyl(trimethylsilyl)methaneboronate
CAS No.:83947-54-0
Molecular Formula:C₁₂H₁₉BO₂Si
Molecular Weight:234.178
Hs Code.:

Synonyms:

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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 ethylene glycol phenyl(trimethylsilyl)methaneboronate

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Technology Process of ethylene glycol phenyl(trimethylsilyl)methaneboronate

There total 2 articles about ethylene glycol phenyl(trimethylsilyl)methaneboronate 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:

: 98-80-6
phenylboronic acid

: 83947-54-0
ethylene glycol phenyl(trimethylsilyl)methaneboronate

Guidance literature:: Multi-step reaction with 2 steps

1: hexane

2: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; hexane;
DOI:10.1021/om00074a005

Reference yield:

: 4406-72-8
2-phenyl[1,3,2]dioxaborolane

: 2344-80-1
Chloromethyltrimethylsilane

: 83947-54-0
ethylene glycol phenyl(trimethylsilyl)methaneboronate

Guidance literature:: With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; sec-BuLi was added dropwise at -78°C to Me3SiCH2Cl in THF, TMEDAadded, stirred 45 min at -78°C, warmed to -55°C, boronatein THF was added, stirred 10 min at -55°C, cooled to -78°C, warmed to 25°C overnight; 2 M ice-cold HCl was added, mixt. extd. with 5:1 Et2O-CH2Cl2, org. phase concd. in vacuo, residue was treated with HOCH2CH2OH and hexane or benzene, refluxed with a Dean-Stark trap, dried over CaCl2, evapd., residuedistilled in vacuo;
DOI:10.1021/om00074a005

Reference yield:

: 83947-54-0
ethylene glycol phenyl(trimethylsilyl)methaneboronate

: 13311-54-1
2,3-dimethyl-2,3-butanediol monohydrate

: 83947-57-3
trimethyl(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)silane

Guidance literature:: In not given; total yield from the two stages (homologation of ethylene glycol benzene boronate with Me3SiCH2Cl in the presence of sec-BuLi and TMEDA followed by transesterification with pinacol) was 76%; elem. anal.;
DOI:10.1021/om00074a005