1-methyl-3-methylenecyclobutanecarbonitrile synthesis
- Product Name:1-methyl-3-methylenecyclobutanecarbonitrile
- CAS Number:32082-16-9
- Molecular formula:C7H9N
- Molecular Weight:107.15
Yield:32082-16-9 96%
Reaction Conditions:
with n-butyllithium;N-ethyl-N,N-diisopropylamine in tetrahydrofuran at -78 - 20; for 2 h;Inert atmosphere;
Steps:
88 1-Methyl-3-oxocyclobutane-1-carbonitrile
To a solution of diisopropylamine (1.30 g, 12.9 mmol) in THF (30 mL) was added 2.5 M n-BuLi (5.15 mL) at about 0° C. The solution was stirred for about 30 min at about 0° C. before being cooled to about -78° C. 3-Methylenecyclobutane-1-carbonitrile (1.00 g, 10.74 mmol) was added and the solution was stirred for about 1 h at about -78° C. Iodomethane (1.98 g, 14.0 mmol) was added to the solution at about -78° C., then the mixture was allowed to warm to about 20° C. and was kept at this temperature for about 0.5 hrs. Saturated aq. NH4Cl (30 mL) was added and the mixture was extracted with EtOAc (3×30 mL). The combined EtOAc extracts were concentrated to afford 1-methyl-3-methylenecyclobutane-1-carbonitrile as a pale yellow oil (1.1 g, 96%).1H NMR (400 MHz, CDCl3) δ: 4.90-4.98 (m, 2H), 3.23-3.35 (m, 2H), 2.64-2.75 (m, 2H), 1.55 (s, 3H).
References:
US2017/240552,2017,A1 Location in patent:Paragraph 0661; 0662
