Formaldehyde → 6-bromo-3,3-bis(hydroxymethyl)-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one

HRID 873703

Reaktionsgleichung

Reaktionsgleichung von HRID 873703
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]2=[O:14].[CH2:15]=[O:16].[C:17]([O-:20])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:12])([CH3:13])[C:6]([CH2:17][OH:20])([CH2:15][OH:16])[C:5]2=[O:14]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 147553646-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

Produkt 1

HCID 867242446-bromo-3,3-bis(hydroxymethyl)-2,2-dimethyl-2,3-dihydro-4H-chromen-4-oneAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a mixture of 6-bromo-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (1.00 g, 3.92 mmol) and dioxane (10 mL) were added formaldehyde (37 wt. % in water, 2.95 mL, 39.2 mmol) and Na2CO3 (831 mg, 7.84 mmol) at room temperature. After stirring overnight at the same temperature, the reaction mixture was filtered. The filtrate was diluted with CHCl3, washed with 1M aqueous HCl and water, dried over MgSO4 and filtered. The filtrate was concentrated at reduced pressure, and the residue was purified with column chromatography on silica gel (hexane-EtOAc, a linear gradient of EtOAc from 0 to 50%) to afford 6-bromo-3,3-bis(hydroxymethyl)-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (1.07 g).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. additionThe filtrate was diluted with CHCl3
  3. washwashed with 1M aqueous HCl and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated at reduced pressure
  7. customthe residue was purified with column chromatography on silica gel (hexane-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-8f6a898fcf4443d6a650731eb9a3951e
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975415B2

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