TETRABUTYLAMMONIUM FLUORIDE synthesis
- Product Name:TETRABUTYLAMMONIUM FLUORIDE
- CAS Number:22206-57-1
- Molecular formula:C16H36FN
- Molecular Weight:261.46
928-90-5
188 suppliers
$8.00/250mg
27329-74-4
1 suppliers
inquiry
22206-57-1
131 suppliers
$5.00/10g
106-93-4
393 suppliers
$15.00/5g
113101-57-8
0 suppliers
inquiry
Yield:113101-57-8 5.38 g (30%)
Reaction Conditions:
with magnesium;pyridinium chlorochromate in tetrahydrofuran;
Steps:
10 Synthesis of 4-(1'-hydroxy-5'-hexynyl)-2,6-di-tert-butylphenol
Example 10 Synthesis of 4-(1'-hydroxy-5'-hexynyl)-2,6-di-tert-butylphenol A mixture of 3.0 g (120 mmol) of magnesium, 25.7 g (72.0 mmol) of 2,6-di- t -butyl-4-bromo-1-trimethylsiloxybenzene and a few drops of 1,2-dibromoethane in 350 mL THF is heated at reflux for two hours and then is cooled to -78° and to it is added 5.78 g (60.0 mmol) of 5-hexynal (which is prepared from the oxidation of 5-hexyn-1-ol using pyridinium chlorochromate). The reaction mixture is stirred at -78° for 15 minutes and then is allowed to warm to 0°, where it is stirred for an additional 30 minutes. The mixture is poured into sat. NH4Cl and the aqueous layer is extracted with pentane. The combined organic phase is washed with sat. NaCl and dried (MgSO4). The crude silylated intermediate is concentrated, dissolved in 300 mL of THF, and treated at room temperature with 28.5 g (90.0 mmol) of tetra- n -butyl-ammonium fluoride trihydrate. After stirring the mixture at 25° for one hour, it is poured into sat. NH4Cl and the layers are separated. The aqueous portion is extracted with pentane and the combined organic phase is washed with sat. NaCl and then dried (MgSO4). The concentrate is purified by flash chromatography (10% EtOAc/hexane, Rf=0.16) and recrystallization (hexane) to afford 5.38 g (30%) of the title compound: mp 70-71°; IR (CCl4) 3620(s), 3310(m), 2960(s), 1430(s), 1160(s), 630(m) cmmin1; 1H-NMR (CDCl3)δ(ppm) 1.40(s, 18H), 1.5-2.3(m, 8H), 4.50(t, 1H), 5.15(s, 1H), 7.10(s, 2H); 13C-NMRδ18.09, 24.88, 30.19, 34.22, 37.69, 68.51, 74.37, 84.25, 122.46, 135.16, 135.75, 153.04 ppm.
References:
EP251408,1991,B1