Water → 4-(2,2-Diethoxyethoxy)benzonitrile

HRID 2219192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2219192
C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)#[N:8].[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17].O>CN(C=O)C.CCOC(C)=O>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][CH:11]=1)[CH3:17]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Produkt 1

HCID 177499644-(2,2-Diethoxyethoxy)benzonitrileAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Powdered potassium carbonate (5.18 g, 37.7 mmol) is added to a stirred solution of 4-cyanophenol (2.00 g, 16.8 mmol) and bromoacetaldehyde diethyl acetal (4.53 mL, 30.3 mmol) in anhydrous DMF (20 mL). The resultant mixture is stirred at 85° C. under nitrogen for 3 days. The mixture is cooled to ambient temperature; then water (100 mL) and EtOAc (100 mL) are added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. The oil is chromatographed on silica (gradient 5-20% EtOAc in hexane) to give 2.80 g (11.9 mmol, 71% yield) of the title compound. 1H NMR (CDCl3): δ1.24 (t, J=7.1 Hz, 6H), 3.60-3.68 (m, 2H), 3.73-3.81 (m, 2H), 4.04 (d, J=5.2 Hz, 2H), 4.83 (t, J=5.2 Hz, 1H), 6.97 (br d, J=9.2 Hz, 2H), 7.58 (br d, J=9.2 Hz, 2H); Analysis for C13H17NO3: calcd: C, 66.36; H, 7.28; N, 5.95; found: C, 66.41; H, 7.34; N, 6.01.

Aufarbeitung

  1. customThe organic layer is separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oil is chromatographed on silica (gradient 5-20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9239dcce5db6453e891a05eb09984c25
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07414063B2

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