Chloroacetonitrile → 5,6-Dimethoxy-2,3-dihydrobenzofuran-2-carbonitrile

HRID 458521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458521
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=O.Cl[CH2:15][C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:13][O:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:2]2[O:1][CH:15]([C:16]#[N:17])[CH2:4][C:3]=2[CH:6]=1

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 109869082-Hydroxy-4,5-dimethoxybenzaldehyde

Produkt 1

HCID 184425025,6-Dimethoxy-2,3-dihydrobenzofuran-2-carbonitrileAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

2-Hydroxy-4,5-dimethoxybenzaldehyde (25.5 g, 0.14 mol), chloroacetonitrile (12.4 g, 0.168 mol) and potassium carbonate (116 g, 0.84 mol) was dissolved in DMF (150 ml). The mixture was stirred for 10 minutes at 165° C. The solvent was concentrated under reduced pressure. The residue was separated in two parts, water was added and the first part was extracted with diethyl ether and the second part extracted with DCM. The second part was evaporated under reduced pressure and dissolved in ether and washed once with water. The organic layers was combined and evaporated under reduced pressure. The crystalline residue was washed with warm methanol (700 ml) and filtered. The residue was dissolved in 225 ml DCM and diethyl ether (450 ml) was added. The crystals formed was collected giving 14.6 g (51% yield) of product. Mp. 162° C.

Aufarbeitung

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customThe residue was separated in two parts, water
  3. additionwas added
  4. extractionthe first part was extracted with diethyl ether
  5. extractionthe second part extracted with DCM
  6. customThe second part was evaporated under reduced pressure
  7. dissolutiondissolved in ether
  8. washwashed once with water
  9. customevaporated under reduced pressure
  10. washThe crystalline residue was washed with warm methanol (700 ml)
  11. filtrationfiltered
  12. dissolutionThe residue was dissolved in 225 ml DCM
  13. additiondiethyl ether (450 ml) was added
  14. customThe crystals formed
  15. customwas collected

Quellen und Nachweise

ORD-Eintrag
ord-7901c477907046e8b02dae7628907b65
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192946B2

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