Sodium Iodide → HCID 20552342, compound

Temperature

-78 °C

The N-benzylidene derivative of glycine ethyl ester, (prepared as described by G. Stork, et al, J. Org. Chem. 41, 3491 (1976)) (30.2 g 158 mmol) in dry tetrahydrafuran (60 ml) was added dropwise to a stirred suspension of potassium t-butoxide (18.1 g, 160 mmol) in dry tetrahydrofuran (60 ml) under nitrogen at -78° C. The solution immediately became bright red in colour. After thirty minutes, sodium iodide (3 g) was added to the solution, followed by the dropwise addition of 1-methanesulphonyloxy-6-cyano-hex-2-yne (the entire product from the previous reaction) in dry tetrahydrofuran (100 ml). The solution was stirred at -78° C. for one hour and allowed to warm up to room temperature over two hours. The solution was stirred for a further three hours then saturated brine (100 ml) and ether (300 ml) were added. The organic layer was washed with brine until neutral and dried over sodium sulphate. Removal of the solvent under reduced pressure (below 30° C.) gave ethyl 2-(benzylidene-amino)-8-cyano-oct-4-ynoate as a red oil.

1. waitAfter thirty minutes
2. temperatureto warm up to room temperature over two hours
3. stirringThe solution was stirred for a further three hours
4. washThe organic layer was washed with brine until neutral and
5. dry with materialdried over sodium sulphate
6. customRemoval of the solvent under reduced pressure (below 30° C.)

ORD record

ord-f20480407a014c548b124fc9aca82594

Source dataset

uspto-grants-1982_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04315022