Sodium borohydride → Tryptophol

HRID 461387Notes

Reaction equation

HRID 461387 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](OCC2C=CC=CC=2)=[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 10564615HCID 10564615, compound

Product 1

HCID 10685Tryptophol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A suspension of benzyl 3-indolylglyoxylate (55.8 g.) and sodium borohydride (22.7 g.) in isopropanol (560 ml.) was heated to reflux over a period of 40 minutes and stirred at that temperature for 4 hours. After cooling the mixture was diluted with water (1.2 l.) and extracted with dichloromethane. The extract was washed with water and the solvent evaporated under reduced pressure to yield a viscous oil. This was distilled at 0.5 - 1 mm. pressure and the friction which distilled at a vapour temperature of 160°-190° was crystallised from toluene (100 ml.), giving the title compound as white crystals, mp. 57°-90°. Yield 24.3 g. (75.5%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux over a period of 40 minutes
  3. temperatureAfter cooling the mixture
  4. extractionextracted with dichloromethane
  5. washThe extract was washed with water
  6. customthe solvent evaporated under reduced pressure
  7. customto yield a viscous oil
  8. distillationThis was distilled at 0.5 - 1 mm
  9. distillationpressure and the friction which distilled at a vapour temperature of 160°-190°
  10. customwas crystallised from toluene (100 ml.)

Sources & evidence

ORD record
ord-c80608a646e04a13849cc1a989ac4a49
Source dataset
uspto-grants-1977_12
Patent number
US04062869

Reaction notes

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