Hydrochloric Acid → 1-(3-Furanyl)-1-propanone

HRID 1780878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1780878
CN(OC)[C:3]([C:5]1[CH:9]=[CH:8][O:7][CH:6]=1)=[O:4].C[Mg]Br.Cl.[CH2:16]1COC[CH2:17]1>CCOCC>[O:7]1[CH:8]=[CH:9][C:5]([C:3](=[O:4])[CH2:16][CH3:17])=[CH:6]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10487090N-methoxy-N-methylfuran-3-carboxamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 150538531-(3-Furanyl)-1-propanoneAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 3-(N-methyl-N-methoxycarbamoyl)furan (14 g, 0.09 mol) in 150 mL of THF cooled to -78° C. was added in portions 36.1 mL (0.108 mol) of 3M methylmagnesium bromide in ether and the mixture was heated to warm to room temperature, and then stirred for 30 min. To the above mixture was added a cold 2N HCl (100 mL) and the aqueous layer was extracted with ether (3×100 mL), the combined organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to yield a pale-yellow oil. The above oil was chromatographed on silica (methylene chloride/hexane 2:1) to afford 6.95 g (70.2 %) of 1-(3-furyl)-1-propanone as a colorless oil which crystallized as a white solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. extractionthe aqueous layer was extracted with ether (3×100 mL)
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto yield a pale-yellow oil
  7. customThe above oil was chromatographed on silica (methylene chloride/hexane 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-8de9d38636514a188275b2bc53365ec1
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05631264

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