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

HRID 461391

Reaction equation

HRID 461391 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-23ec6525c4244b4f9f7f173e7a825fb9
Source dataset
uspto-grants-1977_12
Patent number
US04062869

Linked notes

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