An expeditious, efficient green methodology for the Boc protection of amines and silyl protection of alcohols over tungstophosphoric acid-doped mesoporous silica

Tetrahedron Letters

Volumn 51, Issue 29, 2010, Pages 3855-3858

  Karmakar, Bikash ^a   Banerji, Julie ^b  

^a Gobardanga Hindu College   (India)

^b UNIVERSITY OF CALCUTTA   (India)

Author keywords

Alcohols; Amines; Mesoporous; N Boc; Reusable; Silyl ether

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; CARBAMIC ACID DERIVATIVE; PHOSPHOTUNGSTIC ACID; SILANE DERIVATIVE; SILICON DIOXIDE;

ARTICLE; CATALYST; GREEN CHEMISTRY; POROSITY; REACTION OPTIMIZATION;

EID: 77954311340     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.080     Document Type: Article

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32. 19Tungstophosphoric acid was immobilized over SBA15 matrix by an incipient wet impregnation method. 1.0 mg SBA15 was taken in 20 mL absolute ethanol. Different loadings of TPA (10,15,20 and 30 wt%) was added to it and stirred for 14 h at room temperature. The solution was dried at 60 °C for 2 h and calcined at 550 °C for 4h in aerial atmosphere to furnish a white powder. Characterization data of the catalyst (SEM, TEM, XRD and Fluorescence spectra) are available as Supplementary data.
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34. 2O (1.0 mmol) was stirred in solventless condition in the presence of 50 mg of the TPA/SBA15 catalyst at room temperature. After completion, the reaction mixture was diluted with 5 mL dichloromethane and centrifuged to separate the catalyst for reuse. The filtrate was crystallized to furnish the pure solid in most of the cases.
35. General procedure for the protection of alcohols: A mixture of alcohol (1.0 mmol) and HMDS (1.0 mmol) was stirred in solventless condition in the presence of 50 mg of the TPA/SBA15 catalyst followed by heating at 50 °C. After completion, the reaction mixture was diluted with 5 mL dichloromethane and centrifuged to separate the catalyst for reuse. The filtrate was concentrated under reduced pressure to furnish the pure product. In some cases it was further purified by column chromatography using 60-120 silica gel and ethyl acetate/hexane (4-6%) as eluant
36. All the products were characterized with 1H NMR and IR spectrometry and were compared with the authentic data in the literature.