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ChemicalBook CAS DataBase List TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE

TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE synthesis

4synthesis methods
-

Yield:76782-82-6 100%

Reaction Conditions:

with 1H-imidazole in dichloromethane at 0; for 1.5 h;

Steps:

tert-Butyldimethyl(prop-2-ynyloxy)silane (44)
To a solution of Prop-2-yn-1-ol (43, 1.0 g, 17.84 mmol) and imidazol (1.8 g, 26.76 mmol) in anhydrous CH2Cl2 (50 mL) were added TBSCl (4.0 g, 26.76 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 1.5 h, quenched with saturated NH4Cl, and extracted with Et2O (x 2). The combined organic layers were washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography onsilica gel (n-hexane/AcOEt = 40/1) to give 44 (3.04 g, quant) as a colorless oil.

References:

Higashino, Masato;Ikeda, Naoko;Shinada, Tetsuro;Sakaguchi, Kazuhiko;Ohfune, Yasufumi [Tetrahedron Letters,2011,vol. 52,# 3,p. 422 - 425] Location in patent:supporting information; experimental part

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