Reaktion #72583

Reaktionsgleichung

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

Lösungsmittel

H2SO4

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is heated
2. 2
   Temperaturat reflux for 7 hours
3. 3
   TemperaturAfter refluxing for 18 hours
4. 4
   Einengenthe mixture is concentrated under reduced pressure
5. 5
   Sonstigethe residue obtained
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   TrocknenThe organic phase is dried over magnesium sulphate
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated to dryness
10. 10
    SonstigeThe residue is purified on silica gel (SiO2, eluant: AcOEt)

Vorschrift

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.

Quelle