Reaction #1929020

Reaction equation

NH4Cl

Isopropylmagnesium chloride

2-Bromopyridine

tetraacetyl-(p-formylphenoxy)-β-galactose

→

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

Yield 25.0%

Solvents

THF

THF

Conditions

Workup

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
   DryingThe organic phase is dried over Na2SO4
6. 6
   Otherevaporated under vacuum
7. 7
   OtherThe crude reaction product
8. 8
   Otheris purified by chromatography on silica gel (ether/pentane 2/1 pure ether)
9. 9
   OtherA yellow solid is then obtained (600 mg, yield 25%)

Procedure

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