Cesium carbonate → 1-(4-(4-Isopropoxyphenoxy)-2,6-dimethylphenyl)ethanone

HRID 1465554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465554
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([C:20](=[O:22])[CH3:21])=[C:15]([CH3:23])[CH:14]=1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu](I)I.O>[CH:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([O:12][C:13]2[CH:14]=[C:15]([CH3:23])[C:16]([C:20](=[O:22])[CH3:21])=[C:17]([CH3:19])[CH:18]=2)=[CH:3][CH:4]=1)([CH3:11])[CH3:10]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 2280881-Bromo-4-(propan-2-yloxy)benzeneHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanone

Produkt 1

HCID 866908581-(4-(4-Isopropoxyphenoxy)-2,6-dimethylphenyl)ethanoneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-bromo-4-isopropoxybenzene (16-3, 3.02 g, 14.0 mmol), 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (4-2, 3.54 g, 21.6 mmol), N,N-dimethylglycine HCl salt (0.50 g, 3.5 mmol), copper iodide (0.34 g, 1.8 mmol), and cesium carbonate (9.08 g, 27.9 mmol) in dioxane (30 mL) was heated at 90° C. for 48 h. The reaction mixture was cooled to room temperature, added with water, and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, concentrated under reduced pressure, and purified by column chromatography on silica gel (EtOAc:hexanes=1:20 as eluant) to give 1-(4-(4-isopropoxyphenoxy)-2,6-dimethylphenyl)ethanone (16-4, 2.07 g) as white solids in 79% yield: 1H NMR (500 MHz, CDCl3) δ 6.94 (m, 2 H), 6.87 (m, 2 H), 6.58 (s, 2 H), 4.50 (t, J=6.1 Hz, 1 H), 2.46 (s, 3 H), 2.21 (s, 6 H), 1.34 (s, 6 H), 1.26 (m, 3 H), 0.87 (m, 3 H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography on silica gel (EtOAc:hexanes=1:20 as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-b9814368d938440291184dbd068a0a53
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999983B2

Notizen zur Reaktion

Wird geladen…