2-Bromopropane → 5-Isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene

HRID 1944635

Reaktionsgleichung

Reaktionsgleichung von HRID 1944635
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]=1[OH:13].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:21]([CH3:23])[CH3:22]>CC(C)=O>[CH:21]([O:13][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9]2)([CH3:23])[CH3:22]

Komponenten

5

Edukt 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 574358992-Methoxy-5,6,7,8-tetrahydronaphthalen-1-ol

Produkt 1

HCID 574359005-Isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtaleneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

33 (4.55 g, 25.5 mmol) was charged in a 250 mL round bottom flask, equipped with a reflux condenser, under nitrogen gas. 50 mL of anhydrous acetone was added followed by cesium carbonate (66.55 g, 204.3 mmol). 2-bromopropane (23.94 mL, 255.0 mmol) was added and the reaction mixture was refluxed for 12 h. The solvent was filtered and evaporated in vacuo and purified by flash column chromatography (silica gel, 1:99 EtOAc:Hexanes) to afford 5.2 g (93%) of 5-isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene (34). Rf value: 0.615 (15:85 EtOAc:Hexanes).

Aufarbeitung

  1. customequipped with a reflux condenser, under nitrogen gas
  2. temperaturethe reaction mixture was refluxed for 12 h
  3. filtrationThe solvent was filtered
  4. customevaporated in vacuo
  5. custompurified by flash column chromatography (silica gel, 1:99 EtOAc:Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a9ea7bbfe3004b4ab1736bed4c741164
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394859B2

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