Sodium hydride → 3,4-Dihydro-1-methyl-2-naphthaleneacetonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 7.2 g (0.15 mole) of sodium hydride (50% in oil dispersion) in 200 ml of dimethoxyethane was added dropwise 28.1 g (0.15 mole) of diethylcyanomethylphosphonate [(C2H5O)2P(O)CH2CN]. The addition was complete in ten minutes while the reaction temperature rose to 44° C. The reaction mixture was stirred for 45 minutes and then 25.0 g (0.14 mole) of 1-methyl-2-tetralone was added dropwise over a 30 minute period. The reaction mixture was then warmed at 40° C. for two hours and poured into ice-water. The product was extracted with ether, and the ether extracts were dried over anhydrous magnesium sulfate and concentrated to a yellow oil (31.3 g). The latter was crystallized from ether-hexane to give 3,4-dihydro-1-methyl-2-naphthaleneacetonitrile as a light yellow solid, m.p. 48°-49° C.

Provenance & Evidence