Diisopropylamine → HCID 10657219, compound

Temperature

-78 °C

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.

1. customThe resulting reaction mixture
2. customwas then changed to a 0° C.
3. customThe organic layer was separated
4. washwashed with saturated ammonium chloride (200 ml), saturated sodium chloride (200 ml)
5. dry with materialdried over magnesium sulfate
6. customevaporated to an oil, which
7. customwas purified via column chromatography on 250 g of silica gel
8. washeluted with 5% ether-hexane

ORD record

ord-21cb0917a31f4b62be64802a825ef7f5

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06166031