Hydrochloric Acid → Tryptophol

HRID 461392

反応式

HRID 461392 の反応式
[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

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 899523-Indoleglyoxylyl chlorideHCID 4311764Sodium borohydride

生成物 1

HCID 10685Tryptophol

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8150Diglyme溶媒

実験手順

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°.

後処理

  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.)

出典と根拠

ORDレコード
ord-6af87fd69d0546f1be96be76b1a5f99a
出典データセット
uspto-grants-1977_12
特許番号
US04062869

関連ノート

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