Water → 4,6-dimethyl-N-(alpha-phenylethyl)phenoxazine

Participants

Reaction Conditions

Reaction Steps

A solution of 10 g (34 mmoles) of N-(α-phenylethyl)phenoxazine in 100 ml of anhydrous tetrahydrofuran, under nitrogen, was cooled to -78° C. in a dry ice-acetone bath. 82 ml of a 1.4N solution (114 mmoles) of n-butyl lithium in hexane was slowly added to the cold solution while the temperature was maintained below 0° C. When the addition was completed, the reaction mixture was stirred for 4 hours at 0° C. Then 10.8 g (76 mmoles) of methyl iodide were added, the temperature was maintained at 0°-5° C. The resulting mixture was stirred for 16 hours at 0° C. and then poured into water and extracted with ethyl acetate (3.1 l). The combined extracts were dried and the solvent was removed. The residue purified by column chromatography on 450 g of silica gel, using hexane as eluant afford the pure 4,6-dimethyl-N-(α-phenylethyl)phenoxazine, as an oil, ir: 3837, 2940, 1640, 1600, 1570, 1470 cm-1 : nmr: (CDCl3) 1.90-1.83 ppm (d, 3H), 2.23 ppm (s, 6H), 5.20 ppm (c, 1H), 6.40-6.16 ppm (m, 2H), 6.80-6.53 ppm (m, 4H), 7.53-7.20 ppm (m, 5H).

Provenance & Evidence