Hydrochloric Acid → Tryptophol

HRID 461392

반응식

HRID 461392 반응식
[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

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 899523-Indoleglyoxylyl chlorideHCID 4311764Sodium borohydride

생성물 1

HCID 10685Tryptophol

시약·촉매·용매 2

HCID 962Water용매2회HCID 8150Diglyme용매

실험 절차

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°.

후처리

  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.)

출처 및 근거

ORD 기록
ord-6af87fd69d0546f1be96be76b1a5f99a
출처 데이터셋
uspto-grants-1977_12
특허 번호
US04062869

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