ChemicalBook CAS DataBase List 3-TRIMETHYLSILYL-2-PROPYN-1-OL

3-TRIMETHYLSILYL-2-PROPYN-1-OL synthesis

12synthesis methods

Product Name:3-TRIMETHYLSILYL-2-PROPYN-1-OL
CAS Number:5272-36-6
Molecular formula:C6H12OSi
Molecular Weight:128.24

Tetrahydro-2-[[3-(trimethylsilyl)-2-propyn-1-yl]oxy]-2H-Pyran

36551-06-1

5272-36-6

Compound 5 (0.250 g, 1.17 mmol) was added dropwise to a flask containing methanol (4.0 mL) and Amberlyst-15 (0.025 g) under nitrogen protection at a reaction temperature of 0 °C. The reaction mixture was warmed to 40 °C and stirred for 8 hours. Upon completion of the reaction, the resin was removed by filtration and washed with ethyl acetate (10 mL). To the filtrate, 10% aqueous hydrochloric acid (10 mL) was added, followed by extraction of the organic layer with ethyl acetate (3 x 10 mL). The organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by column chromatography (eluent: hexane/ethyl acetate = 9:1) to afford compound 6 in 96% yield (0.143 g, 1.12 mmol).

36551-06-1
1 suppliers
inquiry

5272-36-6
200 suppliers
$6.00/1g

Yield:5272-36-6 96%

Reaction Conditions:

with Amberlyst 15 in methanol at 0 - 40; for 8 h;Inert atmosphere;

Steps:

3-Trimethylsilyl-prop-2-yn-1-ol (6)²⁹
In a flask containing methanol (4.0 mL) and Amberlyst-15 (0.025 g) under N₂, compound 5 (0.250 g,1.17 mmol) was added dropwise at 0 °C. The mixture was stirred at 40 °C for 8 hr, then the resin was filtered, and washed with ethyl acetate (10 mL). A 10 % aqueous solution of HCl (10 mL) was added and the organic layer was extracted with ethyl acetate (3 × 10 mL), and dried over Na₂SO₄. After concentration, the residue was purified by column chromatography (hexane/ethyl acetate 9:1) to afford compound 6 in 96 % yield (0.143 g, 1.12 mmol).

References:

Moreira, Jardel A.;Neppe, Tiago;De Paiva, Marcelo M.;Deobald, Anna M.;Batista-Pereira, Luciane G.;Paixa?o, Marcio W.;Corre?a, Arlene G. [Journal of the Brazilian Chemical Society,2013,vol. 24,# 12,p. 1933 - 1941]

FullText