Sodium borohydride → 5-Benzyloxy-3-(2-hydroxyethyl)indole

HRID 461391

Reaktionsgleichung

Reaktionsgleichung von HRID 461391
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18](=O)[C:19](OC)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)(C)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 21906905Methyl 2-(5-(benzyloxy)-1H-indol-3-yl)-2-oxoacetate

Produkt 1

HCID 7448495-Benzyloxy-3-(2-hydroxyethyl)indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A suspension of methyl 5-benzyloxyindol-3-ylglyoxylate (10 g.) and sodium borohydride (3.7 g.) in isopropanol (100 ml.) was stirred and refluxed for 5 hours. The cooled mixture was diluted with water and extracted with dichloromethane. Evaporation of the extract gave a pale yellow oil which crystallised from a mixture of toluene and petroleum ether to give 5-benzyloxy-3-(2-hydroxyethyl)indole as a white crystalline powder m.p. 97°-98°.

Aufarbeitung

  1. temperaturerefluxed for 5 hours
  2. extractionextracted with dichloromethane
  3. customEvaporation of the extract
  4. customgave a pale yellow oil which
  5. customcrystallised from a mixture of toluene and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-23ec6525c4244b4f9f7f173e7a825fb9
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04062869

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