Dimethylformamide → 3-Isopropylbenzofuran-2-carbaldehyde

HRID 1362399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362399
[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH:5]=1)([CH3:3])[CH3:2].[Li]CCCC.CN([CH:21]=[O:22])C>C1COCC1>[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[CH:21]=[O:22])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 112174123-IsopropylbenzofuranHCID 178418339Butyllithium

Produkt 1

HCID 577420813-Isopropylbenzofuran-2-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled (0° C.) solution of 3-isopropylbenzofuran (250 mg, 1.56 mmol) in THF (1 mL) is added nBuLi (2 mL, 2 mmol) drop wise and the reaction is stirred for 30 minutes. DMF (1 mL) was added to the reaction and stirred at room temperature overnight. The solution is placed in an ice bath and carefully quenched with 5% aqueous HCl solution (2 mL), and extracted with ethyl acetate (3×5 mL), dried over sodium sulfate and concentrated. The product was purified on silica with 100% hexanes to yield title compound in as a colorless oil (250 mg, 85%): 1H NMR (400 MHz, CDCl3) δ 10.10 (s, 1H), 7.78 (d, 1H, J=9.0 Hz), 7.55 (d, 1H, J=9.0 Hz), 7.32-7.24 (m, 2H), 3.11-3.07 (m, 1H), 1.33-1.31 (2s, 6H).

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. customThe solution is placed in an ice bath
  3. customcarefully quenched with 5% aqueous HCl solution (2 mL)
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified on silica with 100% hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6fc955e1185a4719ae21bbc3218b853c
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

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