3,4-dihydro-2H-pyran → 3-(5-chloro-1H-indol-3-yl)propan-1-ol

HRID 925306

Reaktionsgleichung

Reaktionsgleichung von HRID 925306
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>O.O1CCOCC1.C(OCC)(=O)C>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH:16]=[C:15]2[CH2:14][CH2:13][CH2:12][OH:11]

Komponenten

6

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

Produkt 1

HCID 199793473-(5-chloro-1H-indol-3-yl)propan-1-olAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of (4-chlorophenyl)hydrazine hydrochloride (5.26 g; 28.50 mmol) and 3,4-dihydro-2H-pyran (2.63 mL; 28.50 mmol) in a mixture of water (9 mL) and dioxane (36 mL) was stirred at 100° C. for 48 hours. After cooling to room temperature the mixture was diluted with ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane) to afford 3.85 g (64%) of 3-(5-Chloro-1H-indol-3-yl)propan-1-ol as an oily residue.

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-2bbcde54bbd045b79e1190ebcf378597
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284271B2

Verknüpfte Notizen

Wird geladen…