2-Chloropropane → 4-ISOPROPYLFURAN-2-CARBALDEHYDE

HRID 1363285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363285
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH:10]=[O:11].[CH:12](Cl)([CH3:14])[CH3:13]>C(=S)=S>[CH:12]([C:8]1[CH:7]=[C:6]([CH:10]=[O:11])[O:5][CH:9]=1)([CH3:14])[CH3:13]

Komponenten

5

Edukt 3

HCID 63612-ChloropropaneHCID 7362FurfuralHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 122588064-ISOPROPYLFURAN-2-CARBALDEHYDE

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel

Versuchsvorschrift

To a suspension containing aluminium chloride (24 g, 180 mmol) in 100 mL of CS2 was added 2-furaldehyde (9.8 mL, 156 mmol). To this mixture was added dropwise isopropyl chloride (14.3 mL, 156 mmol), and the resulting mixture stirred at rt for 24 h. The dark mixture was carefully poured into a vigorously stirred 250 g of ice, and then extracted with ether (5×100 mL). The combined organic layers were washed with water, brine, dried (Na2SO4), filtered through a pad of silica gel, and concentrated. The residue was purified by flash chromatography (0-5% EtOAc in heptane) to give 4-isopropylfuran-2-carbaldehyde as an orange oil: Yield 3.5 g (16%). 1H NMR (400 MHz, CDCl3) δ ppm 1.25 (d, J=6.88 Hz, 6H), 2.80-2.91 (m, 1H), 7.16-7.18 (m, 1H), 7.47 (q, J=0.91 Hz, 1H), 9.61 (d, J=0.59 Hz, 1H).

Aufarbeitung

  1. extractionextracted with ether (5×100 mL)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered through a pad of silica gel
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (0-5% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-f8447c41b962472ea717289da12d6718
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884124B2

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