(But-3-en-1-yloxy)(tert-butyl)diphenylsilane synthesis
- Product Name:(But-3-en-1-yloxy)(tert-butyl)diphenylsilane
- CAS Number:135006-32-5
- Molecular formula:C20H26OSi
- Molecular Weight:310.51
627-27-0
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Yield:135006-32-5 100%
Reaction Conditions:
with 1H-imidazole in N,N-dimethyl-formamide at 0 - 20; for 3 h;Inert atmosphere;
Steps:
Compound 5b
Compound 5b Toasolutionof3-buten-1-ol(0.43ml,5mmol,1eq)andimidazole(680.8mg,10mmol,2eq)inDMF(10mL)at0°Cwasaddeddropwisetert-butyldiphenyl-silyl-chloride(1.29mL,6mmol,1.2eq).Thereactionmixturewasallowedtowarmtortandstirredover3h.Water(10mL)wasaddedandtheorganiclayerwasseparated.TheaqueousphasewasextractedwithEt2O(310mL)andthecombinedorganicextractedwerewashedwithsaturatedaqueousNaHCO3(10mL)andbrine(10mL),driedoverMgSO4,andconcentratedunderreducedpressure.Theisolatedproductwaspurifiedbycolumnchromatography(gradient,PE:Et2O95:5)toafford5bbut-3-enyloxy-tert-butyl-diphenyl-silane(1.14g,quantitative)asacolorlessoil.1HNMR(CDCl3,300MHz)δ7.84-7.57(m,4H);7.56-7.32(m,6H);5.86(ddt,J=17.1,10.2,6.9Hz,1H);5.08(dq,J=17.1,1.5Hz,1H);5.03(ddt,J=10.2,1.5,1.0Hz,1H);3.74(t,J=6.7Hz,2H);2.34(qt,J=6.7,1.5Hz,2H);1.08(s,9H).13CNMR(CDCl3,75MHz)δ135.7(CH);135.6(Cq);134.0(C);129.7(CH=);127.7(CH);116.5(=CH2);63.7(CH2O);37.4(CH2);27.0(CH3);19.4(C-Si).HRMS(ESI):m/z:calcdforC20H26OSi[M+Na]+:333.1651,found:333.1653.
References:
Nguyen, Thuy Linh;Ferrié, Laurent;Figadère, Bruno [Tetrahedron Letters,2016,vol. 57,# 47,p. 5286 - 5289] Location in patent:supporting information
![4-{[tert-butyl(diphenyl)silyl]oxy}butan-1-ol](/CAS/20180629/GIF/130372-07-5.gif)
130372-07-5
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135006-32-5
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