Diethyl Ether → N,N-Diphenyl-4-(prop-2-en-1-yl)aniline

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Reaction Conditions

Reaction Steps

To a stirring, anhydrous ether solution (20 mL) of 16 (0.58 g, 1.8 mmol) under inert atmosphere, n-butyl lithium (1.6 M in hexanes, 1.2 mL, 1.92 mmol) was added slowly at −50° C., and the mixture was stirred at −50° C. for 15 min, and gradually warmed up to 25° C. After 3 h, copper iodide(I) (0.51 g, 2.7 mmol) was added followed by dropwise addition of allyl bromide (0.32 g, 2.7 mmol). The solution was stirred for 12 h, followed by quenching with 100 mL saturated aqueous NH4+Cl− solution and extraction with ether (3×100 mL). The combined ether extracts were washed with water (2×100 mL) and brine (2×100 mL), and dried over anhydrous Na2SO4. Following filtration, solvent was removed in vacuum to yield an oil. Chromatography on silica gel with hexane:methylene chloride (4:1) afforded 0.18 g of 17 as a colorless-oil. Yield, 35%. 1H NMR (CDCl3): δ 3.40 (d, J=7.5 Hz, 2H), 5.11-5.32 (m, 2H), 5.98-6.07 (m, 1H), 6.98-7.15 (m, 8H), 7.22-7.37 (m, 6H). Anal. Calcd for C21H19N: C, 88.36; H, 6.72; N, 4.91. Found, C, 88.34; H, 6.10; N, 4.24.

Provenance & Evidence