1,3-Benzodioxole-5-carboxaldehyde, 7-methoxy- → 1-(7-Methoxy-benzo[1,3]dioxol-5-yl)-ethanol

HRID 497023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497023
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH:12]=[O:13])[CH:4]=1.[CH3:14][Mg]Cl>C1COCC1>[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH:12]([OH:13])[CH3:14])[CH:4]=1

Komponenten

4

Edukt 2

HCID 220161,3-Benzodioxole-5-carboxaldehyde, 7-methoxy-HCID 178418332HCID 178418332, Verbindung

Produkt 1

HCID 223181121-(7-Methoxy-benzo[1,3]dioxol-5-yl)-ethanolAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 7-Methoxy-benzo[1,3]dioxole-5-carbaldehyde (I) (1.8 g, 10 mmol) in THF (20 mL) was cooled to −78° C. A solution of methylmagnesium chloride in THF (5.0 mL of 3M, 15 mmol) was added to the solution of i in THF in a dropwise fashion. The reaction was quenched by the addition of HCl (1N, aqueous) and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel; 40%-60% ethyl acetate in hexanes) to afford 2 (0.89 g, 45%).

Aufarbeitung

  1. customThe reaction was quenched by the addition of HCl (1N, aqueous)
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (silica gel; 40%-60% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ef90683692e64b0aa42bc763b7444449
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949544B2

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