Hydrochloric Acid → Tryptophol

HRID 461392

Reaktionsgleichung

Reaktionsgleichung von HRID 461392
[BH4-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](=O)[C:13](Cl)=[O:14])=[CH:4]1.Cl>COCCOCCOC.O>[CH:8]1[CH:9]=[CH:10][C:11]2[NH:3][CH:4]=[C:5]([CH2:12][CH2:13][OH:14])[C:6]=2[CH:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 899523-Indoleglyoxylyl chlorideHCID 4311764Sodium borohydride

Produkt 1

HCID 10685Tryptophol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8150DiglymeLösungsmittel

Versuchsvorschrift

A suspension of sodium borohydride (22.6 g.) in diglyme (800 ml.) was stirred in a jacketted flask with water cooling. 3-Indolylglyoxylyl chloride (41.5 g.) was cautiously added in small portions then the mixture was heated to 95°-100° for 5 hours. The cooled reaction mixture was diluted with water (2 l.), acidified with hydrochloric acid and extracted with dichloroethane. The extract was washed with sodium carbonate solution then with water and evaporated to give crude tryptophol as a brown oil. This was distilled at 0.1 mm and the distillate collected at 155°-160° was crystallised from toluene (50 ml.), giving pure tryptophol as white crystals m.p. 57°-59°.

Aufarbeitung

  1. temperaturethe mixture was heated to 95°-100° for 5 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with dichloroethane
  4. washThe extract was washed with sodium carbonate solution
  5. customwith water and evaporated
  6. customto give crude tryptophol as a brown oil
  7. distillationThis was distilled at 0.1 mm
  8. distillationthe distillate collected at 155°-160°
  9. customwas crystallised from toluene (50 ml.)

Quellen und Nachweise

ORD-Eintrag
ord-6af87fd69d0546f1be96be76b1a5f99a
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04062869

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