Reaktion #62227

Reaktionsgleichung

34

5-isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene

water dioxane

→

35

Ausbeute 71.0%

5-Isopropoxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

Ausbeute 71.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise to the reaction mixture
2. 2
   SonstigeThe solid separated
3. 3
   Filtrationwas filtered
4. 4
   Waschenwashed with ethylacetate
5. 5
   EinengenThe filtrate was concentrated under reduced pressure and 10 mL of saturated sodium bicarbonate solution
6. 6
   workup.ADDITIONwas added
7. 7
   Sonstigethe resulting reaction mixture
8. 8
   Extraktionwas extracted with ether (3×20 mL)
9. 9
   Trocknenthe combined organic phases dried over anhydrous sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Sonstigeevaporated in vacuo
12. 12
    SonstigePurification by flash column chromatography (silica gel, 30:70 EtOAc:Hexanes)

Vorschrift

34 (120 mg, 0.55 mmol) was weighed in a 100 mL round bottom flask and a solution of 5 mL of water:dioxane (5:95) was added and the reaction was set up under nitrogen. A solution of 2,4-dichloro-5,6-dicyanobenzoquinone (0.25 g, 1.09 mmol) dissolved in 5 mL of dioxane was added dropwise to the reaction mixture. The reaction mixture was stirred for 12 h. The solid separated was filtered and washed with ethylacetate. The filtrate was concentrated under reduced pressure and 10 mL of saturated sodium bicarbonate solution was added and the resulting reaction mixture was extracted with ether (3×20 mL) and the combined organic phases dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. Purification by flash column chromatography (silica gel, 30:70 EtOAc:Hexanes) yielded 90 mg (71%) of 35. Rf value: 0.458 (40:60 EtOAc:Hexanes).

Quelle