Dimethylformamide → 2-Benzyloxy-3-(dimethylamino)acrolein

HRID 367004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 367004
P(Cl)(Cl)(Cl)(Cl)Cl.C([O:9][CH:10](OCC)[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C.[CH3:23][N:24]([CH:26]=O)[CH3:25].[OH-].[Na+]>Cl.CCOCC>[CH2:13]([O:12][C:11](=[CH:23][N:24]([CH3:26])[CH3:25])[CH:10]=[O:9])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24819Phosphorus pentachlorideHCID 4321487Benzyloxyacetaldehyde diethyl acetal

Produkt 1

HCID 545210022-Benzyloxy-3-(dimethylamino)acroleinAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Prepared by a modification of the literature procedure reported in Croat. Chim. Acta, 1966, 235. Phosphorus pentachloride (0.13 mol) was added to benzyloxyacetaldehyde diethyl acetal (0.13 mol) at 20-30° C. The reaction mixture was heated at 60° C. for 75 min and then cooled to 0° C. The reaction mixture was treated with DMF (0.39 mol) and stirred at room temperature for four days. The reaction mixture was diluted with 1.0N HCl(aq) (200 ml) and ether (200 ml). The ether layer was discarded and the aqueous layer was basified with 8N NaOH(aq). The aqueous layer was extracted with ethyl acetate and ether and the combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The resulting black oil was purified by column chromatography to give the product as a brown solid (0.06 mol, 43%). δH (250 MHz; CDCl3) 8.62 (1H, s), 7.44-7.26 (5H, m), 6.18 (1H, s), 4.96 (2H, s), 3.04 (6H, s).

Aufarbeitung

  1. customPrepared by a modification of the literature procedure
  2. temperaturecooled to 0° C
  3. extractionThe aqueous layer was extracted with ethyl acetate and ether
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting black oil was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ed877cb23e834ebe854cfc56067d845a
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133255

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