Butyl iodide → 6-Butoxy-2,2-dimethylchroman-4-one

HRID 618821

Reaktionsgleichung

Reaktionsgleichung von HRID 618821
[CH3:1][C:2]1([CH3:14])[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:13])[CH:8]=2)[O:3]1.[H-].[Na+].I[CH2:18][CH2:19][CH2:20][CH3:21]>CN(C=O)C>[CH2:18]([O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:14])([CH3:1])[CH2:11][C:10]2=[O:12])[CH2:19][CH2:20][CH3:21]

Komponenten

5

Edukt 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 35198596-Hydroxy-2,2-dimethylchroman-4-one

Produkt 1

HCID 110540056-Butoxy-2,2-dimethylchroman-4-oneAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 50 g (0.26 mol) of 2,2-dimethyl-6-hydroxychroman-4-one (Example 28a) in 500 ml of DMF was added dropwise to a suspension of 9.0 g (0.3 mol) of 80% sodium hydride in 500 ml of DMF. After stirring at RT for 90 min, 49 g (0.265 mol) of iodobutane were added and the mixture was stirred at RT for a further 90 min. The reaction mixture was then concentrated in vacuo, the residue was treated with water and the mixture was extracted several times with EA. The organic phases were washed with 5 M sodium hydroxide solution, stirred with activated carbon and magnesium sulfate, filtered and concentrated. 57.6 g of 6-butoxy-2,2-dimethylchroman-4-one were obtained.

Aufarbeitung

  1. stirringthe mixture was stirred at RT for a further 90 min
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. additionthe residue was treated with water
  4. extractionthe mixture was extracted several times with EA
  5. washThe organic phases were washed with 5 M sodium hydroxide solution
  6. stirringstirred with activated carbon and magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0e426e1ddffc4afd8e0fc805161a3a1d
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05955607

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