1-(2-Hydroxy4-prop-2-ynyloxy-phenyl)-propan-1-one → 1-(5-hydroxy-2H-chromen-6-yl)-propan-1-one

HRID 606333

Reaktionsgleichung

Reaktionsgleichung von HRID 606333
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[CH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:15])[CH2:13][CH3:14]>C(N(CC)C1C=CC=CC=1)C>[OH:1][C:2]1[C:3]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:4][CH:5]=[C:6]2[C:7]=1[CH:11]=[CH:10][CH2:9][O:8]2

Komponenten

3

Edukt 1

HCID 224828341-(2-Hydroxy4-prop-2-ynyloxy-phenyl)-propan-1-one

Produkt 1

HCID 224828711-(5-hydroxy-2H-chromen-6-yl)-propan-1-oneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7061N,N-DiethylanilineLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-hydroxy-4-prop-2-ynyloxy-phenyl)-propan-1-one (19.8 g, 97 mmol) and N,N-diethylaniline (100 mL) was heated to reflux for 3 h. The reaction mixture was concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 5→10% EtOAc in Hexane) and thereafter recrystallized from EtOAc/Hexane, to give 8.91 g (45%) of 1-(5-hydroxy-2H-chromen-6-yl)-propan-1-one.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe crude product was purified by column chromatography (silica gel, 5→10% EtOAc in Hexane)
  5. customrecrystallized from EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-1c1551a2a13f45a38a5fbbe038148398
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915295B2

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