Réaction #1929020

Équation de réaction

NH4Cl

Isopropylmagnesium chloride

2-Bromopyridine

tetraacetyl-(p-formylphenoxy)-β-galactose

→

tetraacetyl-(p-(pyridinylhydroxymethyl)phenoxy)-β-galactose

Rendement 25.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.WAITthe mixture is left
2. 2
   workup.WAITThe mixture is left
3. 3
   workup.STIRRINGstirring for 18 h
4. 4
   ExtractionThe resulting aqueous solution is extracted with ethyl acetate
5. 5
   SéchageThe organic phase is dried over Na2SO4
6. 6
   Autreevaporated under vacuum
7. 7
   AutreThe crude reaction product
8. 8
   Autreis purified by chromatography on silica gel (ether/pentane 2/1 pure ether)
9. 9
   AutreA yellow solid is then obtained (600 mg, yield 25%)

Mode opératoire

2-Bromopyridine (726 mg, 440 μl, 4.6 mmol) is dissolved in 5 ml of THF at ambient temperature. Isopropylmagnesium chloride (2.3 ml, 4.6 mmol, 2M in THF) is added dropwise under argon and the mixture is left stirring for 2 hours. This solution is added to a solution of tetraacetyl-(p-formylphenoxy)-β-galactose (2.07 g, 4.6 mmol) in 3 ml of THF at ambient temperature. The mixture is left stirring for 18 h and then a saturated NH4Cl solution is slowly added. The resulting aqueous solution is extracted with ethyl acetate. The organic phase is dried over Na2SO4 and evaporated under vacuum. The crude reaction product is purified by chromatography on silica gel (ether/pentane 2/1 pure ether). A yellow solid is then obtained (600 mg, yield 25%).

Source