Reaktion #1929020

Reaktionsgleichung

NH4Cl

Isopropylmagnesium chloride

2-Bromopyridine

tetraacetyl-(p-formylphenoxy)-β-galactose

→

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

Ausbeute 25.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle