Sodium borohydride → Tryptophol

HRID 461388Notes

Reaction equation

HRID 461388 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=O)[C:11](OCC(C)C)=[O:12])=[CH:2]1.[BH4-].[Na+]>C(O)(C)C.O>[OH:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21393605HCID 21393605, compound

Product 1

HCID 10685Tryptophol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A stirred suspension of isobutyl 3-indolylglyoxylate (48.5 g.) and sodium borohydride (22.7 g.) in isopropanol (500 ml.) was slowly heated to reflux and held for 5 hours. The cooled mixture was diluted with water (2 l.) and extracted with dichloromethane. The extract was washed with water, dried over magnesium sulphate and concentrated under reduced pressure to an oil which crystallised on cooling. Recrystallisation from toluene (100 ml.) gave 3-(2-hydroxyethyl)indole as a cream-coloured crystalline powder, mp. 55°-56°. Yield 23.3 g. (72.3%).

Workup

  1. temperaturewas slowly heated
  2. temperatureto reflux
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure to an oil which
  7. customcrystallised
  8. temperatureon cooling
  9. customRecrystallisation from toluene (100 ml.)

Sources & evidence

ORD record
ord-02e4f85747e34047833a7b13fa31a5f6
Source dataset
uspto-grants-1977_12
Patent number
US04062869

Reaction notes

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