Hydrochloric Acid → Tryptophol

HRID 461390

反応式

HRID 461390 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=O)[C:11](OC2C=CC=C(C)C=2)=[O:12])=[CH:2]1.[BH4-].[Na+].Cl.C1(C)C(O)=CC=CC=1>C(O)(C)C.O>[CH:6]1[CH:7]=[CH:8][C:9]2[NH:1][CH:2]=[C:3]([CH2:10][CH2:11][OH:12])[C:4]=2[CH:5]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 335O-CresolHCID 4311764Sodium borohydrideHCID 21393607m-Cresyl 3-indolylglyoxylate

生成物 1

HCID 10685Tryptophol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

A stirred suspension of m-cresyl 3-indolylglyoxylate (55.8 g.) and sodium borohydride (22.7 g.) in isopropanol (300 ml.) was slowly heated to reflux and held for 5 hours. The cooled mixture was diluted with water (2 l.), acidified with hydrochloric acid and extracted with dichloromethane. The extract was washed with sodium carbonate solution, dried and evaporated to give a mobile oil smelling strongly of cresol. This was distilled at 0.5 - 1 mm and the fraction collected at 160°-200° vapour temperature was crystallised from toluene (60 ml.), giving tryptophol as white crystals m.p. 57°-59°.

後処理

  1. temperaturewas slowly heated
  2. temperatureto reflux
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with sodium carbonate solution
  5. customdried
  6. customevaporated
  7. customto give a mobile oil
  8. distillationThis was distilled at 0.5 - 1 mm
  9. customthe fraction collected at 160°-200° vapour temperature
  10. customwas crystallised from toluene (60 ml.)

出典と根拠

ORDレコード
ord-27be99fc67444f7b85e6124d4e37343f
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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