Acetonitrile → 3-(Naphthalen-1-yl)-3-oxopropanenitrile

HRID 928242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928242
C([Li])CCC.CCCCCC.[C:12](#[N:14])[CH3:13].[C:15]1([C:25](OCC)=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>O1CCCC1>[C:15]1([C:25]([CH2:13][C:12]#[N:14])=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8058HexaneHCID 76364Ethyl 1-naphthoateHCID 178418339Butyllithium

Produkt 1

HCID 219434673-(Naphthalen-1-yl)-3-oxopropanenitrileAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2.50 M of n-butyllithium in hexane (49.9 mL, 125 mmol) in tetrahydrofuran (49.9 mL) cooled to −78° C. is added acetonitrile (6.52 mL, 125 mmol) drop-wise. The resulting cloudy mixture is stirred for 30 min. Ethyl α-napthoate (8.87 mL, 49.9 mmol) is added drop-wise and the reaction mixture is stirred at −78° C. for 2 hr. The reaction is warmed to room temperature, quenched with acetic acid (50 ml) and partitioned between ethyl acetate and water. The organic layer is dried over Na2SO4, filtered and concentrated in vacuo. The crude material is purified by column chromatography (eluent: 5-15% CH2Cl2/methanol) to provide 1-naphthoylacetonitrile (6.99 g, yield 72%). 1H NMR (400 MHz, CDCl3) δ 8.82 (d, J=8.7 Hz, 1H), 8.11 (d, J=8.3 Hz, 1H), 7.90 (t, J=8.1 Hz, 2H), 7.71-7.64 (m, 1H), 7.57 (dt, J=15.5, 7.2 Hz, 2H), 4.21 (s, 2H).

Aufarbeitung

  1. stirringthe reaction mixture is stirred at −78° C. for 2 hr
  2. customquenched with acetic acid (50 ml)
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material is purified by column chromatography (eluent: 5-15% CH2Cl2/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-7a0ccae401454707b989490608e1fc1f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290500B2

Notizen zur Reaktion

Wird geladen…