Reaktion #59434
ord-d7ace11d3202418a94aa69cd11dd3dc1
Reaktionsgleichung
Reagenzien
Lösungsmittel
Reaktionsbedingungen
Aufarbeitung
- 1Sonstigea precipitate was formed
- 2TemperaturThe reaction mixture was heated
- 3Temperaturat reflux for 16 hours
- 4FiltrationIt was then filtered
- 5Sonstigeto remove the precipitate
- 6Einengenconcentrated under reduced pressure
- 7Sonstigesolid sodium bromide was removed by filtration
- 8WaschenThe dichloromethane filtrate was then washed with water (100 ml) and brine (100 ml)
- 9SonstigeThe organic layer was collected
- 10Trocknendried over magnesium sulphate
- 11Einengenconcentrated under reduced pressure
- 12Sonstigeto give an orange solid
- 13Filtrationfiltered off
Vorschrift
Sodium hydride (60% dispersion in oil, 3.43 g, 86 mmol) was added to a solution of 3,5-heptanedione (10 g, 78 mmol), in 2-butanone (200 ml), under nitrogen. A slight exotherm was observed during gas evolution. Sodium iodide (11.7 g, 78 mmol) was then added, followed by 4-cyanobenzyl bromide (15.29 g, 78 mmol) in 2-butanone (20 ml) and a precipitate was formed. The reaction mixture was heated at reflux for 16 hours. It was then filtered to remove the precipitate and concentrated under reduced pressure. The residue was stirred in dichloromethane (100 ml) and solid sodium bromide was removed by filtration. The dichloromethane filtrate was then washed with water (100 ml) and brine (100 ml). The organic layer was collected, dried over magnesium sulphate and concentrated under reduced pressure to give an orange solid. This was slurried in diethyl ether and filtered off to provide the title compound (11.01 g, 58%) as a pale yellow solid. 1H-NMR (400 MHz, CDCl3): δ=0.98 (t, 6H), 2.29-2.35 (m, 2H), 2.42-2.52 (m, 2H), 3.19 (d, 2H), 3.97 (t, 1H), 7.25 (d, 2H), 7.56 (d, 2H); LRMS: APCl−: m/z 242 [M−H].