Iodoethane → Methyl 4-(3-cyanopentan-3-yl)benzoate

HRID 404104

Reaktionsgleichung

Reaktionsgleichung von HRID 404104
C[C:2]([CH3:5])([O-])C.[K+].[CH2:7](I)[CH3:8].[C:10]([CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)#[N:11]>C1COCC1>[C:10]([C:12]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)([CH2:2][CH3:5])[CH2:7][CH3:8])#[N:11]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 848548Methyl 4-(cyanomethyl)benzoateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 67150320Methyl 4-(3-cyanopentan-3-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of potassium tert-butoxide (4.81 g) in THF (15 mL) at −30° C. was added a solution of ethyl iodide (4.11 mL) and methyl 4-(cyanomethyl)benzoate (3 g) THF (15 mL) under nitrogen atmosphere over 20 min. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched by the addition of water (10 mL) and ethyl acetate was added. The organic layer was washed successively with water, brine and dried over anhydrous sodium sulfate. The organic solvent was removed to obtain a residue, which was purified by column chromatography (silicagel, 20% ethyl acetate in petroleum ether) to obtain a crude solid. The crude solid was crystallized using chloroform in petroleum ether to afford the title compound.

Aufarbeitung

  1. customThe reaction was quenched by the addition of water (10 mL) and ethyl acetate
  2. additionwas added
  3. washThe organic layer was washed successively with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe organic solvent was removed
  6. customto obtain a residue, which
  7. customwas purified by column chromatography (silicagel, 20% ethyl acetate in petroleum ether)
  8. customto obtain a crude solid
  9. customThe crude solid was crystallized

Quellen und Nachweise

ORD-Eintrag
ord-f1efd629e5534efeae474dc7bd1d1da7
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748426B2

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