1,4-Dioxane--water (1/1) → 5-Isopropoxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

HRID 33949

Reaktionsgleichung

Reaktionsgleichung von HRID 33949
[CH:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10]2)([CH3:3])[CH3:2].O.[O:18]1CCOCC1>O1CCOCC1>[CH:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]2=[O:18])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 218864351,4-Dioxane--water (1/1)HCID 574359005-Isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene

Produkt 1

HCID 574359025-Isopropoxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-oneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. additionwas added dropwise to the reaction mixture
  2. customThe solid separated
  3. filtrationwas filtered
  4. washwashed with ethylacetate
  5. concentrationThe filtrate was concentrated under reduced pressure and 10 mL of saturated sodium bicarbonate solution
  6. additionwas added
  7. customthe resulting reaction mixture
  8. extractionwas extracted with ether (3×20 mL)
  9. dry with materialthe combined organic phases dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customPurification by flash column chromatography (silica gel, 30:70 EtOAc:Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-765e7f3a30eb460182dadf93c7120c6d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429681B2

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