Diethyl Ether → HCID 10494674, compound

Participants

Reaction Steps

To a cooled (ice bath) 2M diethyl ether solution of 4-tert-butylphenylmagnesium bromide (15 ml, 0.03 mmol) was added dropwise under argon 15 ml of a tetrahydrofuran solution of 6-isopropylquinoline (5.13 g, 0.03 mol). The resulting mixture was refluxed for 5 hours, stirred at room temperature for 12 hours and quenched with water (80 ml). The yellow precipitate obtained was then filtered and washed with hexane. Crystallization in hexane:chloroform 40:1 yielded 3.7 g of pure (±)-2-(4-tert-butylphenyl)-6-isopropylquinoline (40% yield). 1H NMR(CDCl3): 8.2 (m, ArH, 4H), 7.84 (m, ArH, 1H), 7.60 (m, ArH, 4H), 3.12 (s, CH(Me)2, 1H), 1.4 (s, CH(Me)2 and C(Me)3, 15H); Mass/Cl—NH3: MH− 304.

Provenance & Evidence