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

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).

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

ORD record

ord-255f8ac0213449be83b6a42f3e3aad98

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586441B2