反応 #72583

反応方程式

B(OMe)3

LiBr

NaBH4

NaCl

compound

Ethyl (2-oxo-2,3-dihydro-1H-indol-5-yl)acetate

→

title product

5-(2-Hydroxyethyl)-1,3-dihydro-2H-indol-2-one

溶媒

H2SO4

THF

反応条件

後処理

1. 1
   温度The reaction mixture is heated
2. 2
   温度at reflux for 7 hours
3. 3
   温度After refluxing for 18 hours
4. 4
   濃縮the mixture is concentrated under reduced pressure
5. 5
   その他the residue obtained
6. 6
   抽出extracted with ethyl acetate
7. 7
   乾燥The organic phase is dried over magnesium sulphate
8. 8
   ろ過filtered
9. 9
   その他evaporated to dryness
10. 10
    その他The residue is purified on silica gel (SiO2, eluant: AcOEt)

実験手順

LiBr (1.03 g) is added to a solution of NaBH4 (0.45 g) in THF (15 ml). The reaction mixture is heated at reflux for 7 hours, and the compound obtained in Step B (1.3 g) is added, followed by B(OMe)3 (0.067 ml). After refluxing for 18 hours, the mixture is concentrated under reduced pressure and the residue obtained is taken up in 20 ml of 3N H2SO4. The aqueous phase is saturated with NaCl and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness. The residue is purified on silica gel (SiO2, eluant: AcOEt) to yield the title product in the form of a beige solid. The compound obtained is used directly in the next reaction.

出典