Tetrahydrofuran → HCID 69673663, compound

Participants

Reaction Steps

N-[3-(4-Methyl-benzoyl)-5,6,7,8-tetrahydro-naphthalen-2-yl]-benzamide was prepared by a modification of the route described in Okabe, M. and Sun, R. C.; Tetrahedron 1995, 51(7), 1861-1866). To a 100 mL flask containing a solution 2-phenyl-6,7,8,9-tetrahydro-naphtho[2,3-d][1,3]oxazin-4-one (220 mg, 0.793 mmol) in dichloromethane (20 mL) under nitrogen and cooled to −78 C was added dropwise by syringe p-tolylmagnesium bromide solution in tetrahydrofuran (1.0 M, 0.87 mL, 0.87 mmol) and the yellow solution was allowed to warm to room temperature overnight with stirring. Reaction had not proceeded to completion and was re-cooled to −78 C and added more p-tolylmagnesium bromide solution (0.30 mL, 0.38 eq) and transferred the reaction to an acetonitrile-CO2 bath (−42 C) and stirred for 1 hour. Quenched by addition of saturated ammonium chloride solution (2 mL) and allowed to warm to ambient temperature. Diluted further with water (10 mL) and the organic fraction was removed using a hydrophobic frit, evaporated onto silica gel, and chromatographed using ISCO Companion with a Redisep silica gel 40 g cartridge and a gradient of heptane and ethyl acetate (0% to 20%). Evaporation gave N-[3-(4-methyl-benzoyl)-5,6,7,8-tetrahydro-naphthalen-2-yl]-benzamide as a pale yellow solid 191.4 mg (65.3% Yield). LCMS (5 min acidic) 3.52 min 100% pure by ELSD and UV ES+ 370. HNMR (CDCl3) >95% pure 11.69 (s, 1H), 8.08-8.06 (m, 2H), 7.65-7.63 (m, 2H), 7.55-7.48 (m, 3H), 7.33-7.29 (m, 3H), 2.92-2.89 (m, 2H), 2.71-2.68 (m, 2H), 2.46 (s, 3H), 1.87-1.79 (m, 4H).

Provenance & Evidence