Hexane → 3,4-Dihydro-2-naphthalenylacetonitrile

Participants

Reaction Steps

To a mechanically stirred mixture of hexane washed sodium hydride (8.98 g, 0.187 mol, 50%/mineral oil) in THF (400 mL) was added diethyl cyanomethylphosphonate (33.13 g, 0.187 mol) dropwise. The reaction was stirred at room temperature for 1/2 hour. β-Tetralone (24.8 g, 0.170 mol) in THF (100 mL) was added dropwise at 0° C., and the reaction was stirred at room temperature for 1 hour. The reaction was diluted with water (600 mL) and extracted with ether (3×400 mL). The organic phase was washed with brine, dried (MgSO4), and concentrated under reduced pressure to give an orange oil. Distillation from bulb to bulb under high vacuum yielded 22.65 g (79%) of product as a pale yellow oil.

Provenance & Evidence