Acetonitrile → 3-Amino-3-(2-furyl)acrylonitrile

HRID 1356020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356020
[C:1](#[N:3])[CH3:2].C([Li])CCC.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]#[N:15]>C1COCC1>[NH2:15][C:14]([C:10]1[O:9][CH:13]=[CH:12][CH:11]=1)=[CH:2][C:1]#[N:3]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 692452-FuronitrileHCID 178418339Butyllithium

Produkt 1

HCID 692835483-Amino-3-(2-furyl)acrylonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the method of Gupta et al. (Tetrahedron 1990, 46, 3703) and Bullock and Gregory (Can. J. Chem. 1965, 43, 332), to a stirred solution of 0.53 ml (10.0 mmol) acetonitrile in 25 ml dry THF under argon at −78° C. was added 6.25 ml (10.0 mmol) n-butyllithium solution (1.6M in hexane) and stirring continued for 15 minutes. 0.87 ml (10.0 mmol) 2-furonitrile was then added dropwise and stirring continued for 45 minutes at −78° C. The reaction mixture was quenched at 0° C. with 3 ml water and then partitioned between ether and water. The organic phase was then washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 1.10 g (82%) (E or Z)-3-amino-3-furan-2-yl-acrylonitrile as a yellow crystalline solid which was stored in the refrigerator. EI-MS m/e (%): 134 (M+, 100).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 45 minutes at −78° C
  3. customThe reaction mixture was quenched at 0° C. with 3 ml water
  4. custompartitioned between ether and water
  5. washThe organic phase was then washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-255f8ac0213449be83b6a42f3e3aad98
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586441B2

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