Iodoethane → 3-Ethoxy-5-ethyl-2-fluorobenzaldehyde

HRID 1438158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1438158
[Si]([O:8][C:9]1[C:10]([F:19])=[C:11]([CH:14]=[C:15]([CH2:17][CH3:18])[CH:16]=1)[CH:12]=[O:13])(C(C)(C)C)(C)C.[F-].[K+].I[CH2:23][CH3:24]>CN(C=O)C.CCOC(C)=O>[CH2:23]([O:8][C:9]1[C:10]([F:19])=[C:11]([CH:14]=[C:15]([CH2:17][CH3:18])[CH:16]=1)[CH:12]=[O:13])[CH3:24]

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 522689Potassium FluorideHCID 598380723-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde

Produkt 1

HCID 579428023-Ethoxy-5-ethyl-2-fluorobenzaldehydeAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 118C (244 mg, 0.87 mmol) in DMF (2.0 mL) was added potassium fluoride (100 mg) and iodoethane (0.13 mL). The mixture was stirred at rt overnight. It was diluted with EtOAc and the organic extracts were washed with brine and dried. The crude product was purified by column chromatography to give 118D (158 mg, 100% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.22 (t, J=7.69 Hz, 3H) 1.46 (t, J=7.03 Hz, 3H) 2.62 (q, J=7.47 Hz, 2H) 4.13 (q, J=7.03 Hz, 2H) 7.02 (dd, J=7.91, 2.20 Hz, 1H) 7.22 (dd, J=5.27, 2.20 Hz, 1H) 10.35 (s, 1H).

Aufarbeitung

  1. washthe organic extracts were washed with brine
  2. customdried
  3. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5d5db87ccb1747ba9fae5a82e0bda9b6
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622585B2

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