Water → 5-(benzyloxy)-2,3-dihydro-1H-inden-1-one

HRID 278437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 278437
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2331475-Hydroxy-1-indanone

Produkt 1

HCID 107524065-(benzyloxy)-2,3-dihydro-1H-inden-1-oneAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 5-hydroxy-indan-1-one (5.3 g, 35.7 mmol), KJ (0.6 g, 3.6 mmol) and K2CO3 (6.17 g, 44.6 mmol) and benzyl bromide (4.66 ml, 39.3 mmol) in DMF (50 ml) were heated at 100° C. for 1 hr. Addition of H2O (150 ml) and extraction with EtOAc (3×50 ml), washing the organic phase with satd. NaCl solution (100 ml) and drying with MgSO4 and evaporation afforded a brown solid. This material was recrystallised twice from EtOH to afford 5-benzyloxy-indan-1-one (6 g, 25.17 mmol, 70%) as yellow crystals, Mp. 105-106° C., MS m/e=238.1 (M+).

Aufarbeitung

  1. washwashing the organic phase with satd
  2. dry with materialNaCl solution (100 ml) and drying with MgSO4 and evaporation
  3. customafforded a brown solid
  4. customThis material was recrystallised twice from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-99c56832d9ff4460af9ad6568e2c193c
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359138B1

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