تفاعل #172400

معادلة التفاعل

sodium hydroxide

hydrogen peroxide

9-borabicyclo[3.3.1]nonane

compound

3-Allyl-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

sodium bisulphite

→

3-(3-Hydroxypropyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

المذيبات

water

THF

THF

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىdoes not exceed 30° C
2. 2
   workup.STIRRINGThe mixture is stirred with ice-
3. 3
   درجة الحرارةcooling for 30 min
4. 4
   أخرىThe organic phase is separated off
5. 5
   استخلاصthe aqueous phase is extracted twice with ethyl acetate
6. 6
   غسيلThe combined organic phases are washed with saturated aqueous sodium chloride solution
7. 7
   تجفيفThe organic phase is dried over sodium sulphate
8. 8
   أخرىevaporated to dryness under reduced pressure
9. 9
   أخرىThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:4)

الإجراء التجريبي

At 0° C., 18.5 ml (9.25 mmol) of a 0.5 molar solution of 9-borabicyclo[3.3.1]nonane in THF are slowly added dropwise to 1.00 g (3.70 mmol) of the compound from Example 35A in 4 ml THF. After one hour at room temperature, the mixture is again cooled to 0° C., and 18.5 ml (18.5 mmol) of a 1 molar solution of sodium hydroxide in water are added dropwise. The mixture is stirred at 0° C. for a further 30 min, and 3.24 ml of a 30% strength hydrogen peroxide solution are then added such that the temperature does not exceed 30° C. The mixture is stirred with ice-cooling for 30 min, and ethyl acetate and then 11 g (40 mmol) of sodium bisulphite solution are then added. The organic phase is separated off, and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate and then evaporated to dryness under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:4). This gives 1.03 g (83% of theory) of the desired product.

المصدر