Phenethyl bromide → 6-(2-Phenylethoxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1847192

Reaktionsgleichung

Reaktionsgleichung von HRID 1847192
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.Br[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:16]1([CH2:15][CH2:14][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Produkt 1

HCID 130673316-(2-Phenylethoxy)-1,2,3,4-tetrahydronaphthalen-1-oneAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 6-hydroxy-3,4-dihydro-1(2H)-naphthalenone (2.0 g, 12.3 mmol) and (2-bromoethyl)benzene (4.8 g, 25.8 mmol) in ACN (20 mL) was added potassium carbonate (3.4 g, 24.6 mmol) at rt. The solution was heated at reflux overnight. The reaction was filtered, concentrated, and purified by silica gel chromatography (PE/EtOAc/DCM=10:1:2) to give 2.0 g (61%) of the title compound as a brown oil. 1H NMR (300 MHz, CDCl3): δ 2.08-2.16 (2H, m), 2.62 (2H, t, J=6.3 Hz), 2.92 (2H, t, J=6.3 Hz), 3.13 (2H, t, J=7.2 Hz), 2.92 (2H, t, J=7.2 Hz), 6.71 (1H, d, J=2.1 Hz), 6.83 (1H, dd, J=2.4, 8.7 Hz), 7.27-7.38 (5H, m), 8.01 (1H, dd, J=8.7 Hz).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (PE/EtOAc/DCM=10:1:2)

Quellen und Nachweise

ORD-Eintrag
ord-43360678a19e486a907c35c5920027e4
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952151B2

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