Allyl bromide → 7-Allyloxy-2,2-dimethyl-4-oxochroman

HRID 494941

Reaktionsgleichung

Reaktionsgleichung von HRID 494941
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[CH2:7][C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C)C=O.C(OCC)(=O)C>[CH2:23]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[CH2:7][C:8]([CH3:12])([CH3:13])[O:9]2)=[CH:4][CH:3]=1)[CH:22]=[CH2:21]

Komponenten

6

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 6009027-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

Produkt 1

HCID 156096387-Allyloxy-2,2-dimethyl-4-oxochromanAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

9.74 g of 7-hydroxy-2,2-dimethyl-4-oxochroman (CAS#: 17771-33-4) was dissolved in 150 ml of N,N-dimethylformamide. Thereafter, 10.5 g of potassium carbonate and 7.36 g of allyl bromide were added to the reaction solution, and the obtained mixture was stirred at room temperature overnight. Thereafter, the reaction solution was diluted with ethyl acetate, and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was then purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 11.0 g of the subject compound.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was then purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-668aede295db45608e75dc2a589888e8
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538123B2

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