ChemicalBook CAS DataBase List 2-(TRIMETHYLSILYLOXY)FURAN

2-(TRIMETHYLSILYLOXY)FURAN synthesis

5synthesis methods

Product Name:2-(TRIMETHYLSILYLOXY)FURAN
CAS Number:61550-02-5
Molecular formula:C7H12O2Si
Molecular Weight:156.25

Accessible by silylation of 2(5H)-furanone, which is obtained at very low cost by oxidation of furfural.

75-77-4
563 suppliers
$5.04/10

497-23-4
228 suppliers
$6.00/1g

61550-02-5
66 suppliers
$60.00/100mg

Yield: 88%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20;Inert atmosphere;

Steps:

(furan-2-yloxy)trimethylsilane (2)
To a solution of 2(5H)-furanone (16.9 mL, 238 mmol, 1.0 eq.) in DCM (170 mL, 1.4 M) at 0 °Cwas added triethylamine (33.7 mL, 285 mmol, 1.2 eq.). Then chlorotrimethylsilane (37.4 mL, 250 mmol, 1.05 eq.) was added dropwise to the resulting red brown solution at the same temperature. The suspension was stirred overnight at room temperature. The reaction was diluted with 100 mL pentane and filtered through a frit funnel into a second flask containing 100 mL pentane. The solution was filtered again then concentrated under reduced pressure to give a red brown oil. (If precipitation formed during concentration, immediately dilute it with pentane and filter the solution again.) The crude product was distilled under vacuum (ca. 100 mbar, 105 °C oil bath) to furnish 2 (32.6 g) as a colorless oil in 88% yield.

References:

Li, Liubo;El Khoury, Anton;Clement, Brennan O.;Harran, Patrick G. [Tetrahedron Letters,2021,vol. 72,art. no. 153056] Location in patent:supporting information

27607-77-8 Synthesis