Diisopropylamine → HCID 10657219, compound

Participants

Reaction Conditions

Reaction Steps

To a -78° C. solution of lithium diisopropyl amide [from 4.37 ml (31.2 mmol) of diisopropyl amine in 28 ml tetrahydrofuran and 11.9 ml (29.8 mmol) of 2.5M n-butyllithium] was slowly added (over 15 minutes) a solution of 5.00 g (28.4 mmol) of 3,4-dihydro-7-methoxy-1(2H)-naphthalenone in 10 ml tetrahydrofuran. The resulting reaction mixture was stirred 10 minutes at -78° C. The cooling bath was then changed to a 0° C. ice-water bath, and was immediately followed by the rapid addition of 3.98 ml (35 mmol) of n-butyl iodide. Hexamethylphosphoramide (10.4 ml, 60 mmol) was then added and the resultant solution atirred at 25° C. for 2 hours. The reaction was added to a mixture of 200 ml saturated ammonium chloride and 300 ml ether. The organic layer was separated, washed with saturated ammonium chloride (200 ml), saturated sodium chloride (200 ml), dried over magnesium sulfate and evaporated to an oil, which was purified via column chromatography on 250 g of silica gel eluted with 5% ether-hexane to give 1.6 g (24%) of present title product as an oil.

Provenance & Evidence