تفاعل #1929020

معادلة التفاعل

NH4Cl

Isopropylmagnesium chloride

2-Bromopyridine

tetraacetyl-(p-formylphenoxy)-β-galactose

→

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

المردود 25.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر