Реакция #1929020

Уравнение реакции

NH4Cl

Isopropylmagnesium chloride

2-Bromopyridine

tetraacetyl-(p-formylphenoxy)-β-galactose

→

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

Выход 25.0%

Растворители

THF

THF

Условия реакции

Обработка

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

Методика

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%).

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