反応 #172389

反応方程式

hydrogen peroxide

9-borabicyclo[3.3.1]nonane

compound

1-(2-Methoxy-4-nitrophenyl)-3-vinylpyridin-2(1H)-one

sodium disulphite

sodium hydroxide

→

3-(2-Hydroxyethyl)-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.WAITAfter a further hour at this temperature
2. 2
   その他does not exceed 30° C
3. 3
   温度Cooling
4. 4
   その他is removed
5. 5
   workup.STIRRINGthe mixture is stirred for another 30 min
6. 6
   抽出The mixture is extracted repeatedly with ethyl acetate
7. 7
   その他the organic phase is separated off
8. 8
   洗浄The combined organic phases are washed with saturated sodium chloride solution
9. 9
   乾燥dried over magnesium sulphate
10. 10
    その他evaporated to dryness under reduced pressure
11. 11
    その他The residue is absorbed on silica gel
12. 12
    その他chromatographed
13. 13
    その他evaporated to dryness under reduced pressure
14. 14
    その他For crystallization, tert-butyl methyl ether
15. 15
    workup.ADDITIONis added
16. 16
    ろ過The crystals are filtered off
17. 17
    その他dried under reduced pressure

実験手順

At 0° C., a solution of 36 g (299 mmol) of 9-borabicyclo[3.3.1]nonane in 600 ml of tetrahydrofuran is added over a period of 45 min to 37 g (136 mmol) of the compound from Example 20A. After a further hour at this temperature, a solution of 27 g (680 mmol) of sodium hydroxide (1N in water) is added over the course of 15 min. The mixture is stirred for a further 5 min, and 125 ml of a 30% strength hydrogen peroxide solution are then added such that the temperature does not exceed 30° C. Cooling is removed, and the mixture is stirred for another 30 min. The mixture is extracted repeatedly with ethyl acetate, the combined organic phases are washed with a solution of 730 g (1.50 mol) of sodium disulphite, the organic phase is separated off and the aqueous phase is reextracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue is absorbed on silica gel and chromatographed using a gradient of cyclohexane and ethyl acetate. The product fractions are combined and evaporated to dryness under reduced pressure. For crystallization, tert-butyl methyl ether is added. The crystals are filtered off and dried under reduced pressure. This gives 24 g (60% of theory) of the desired product.

出典