Diethyl Ether → HCID 86741649, compound

Participants

Reaction Conditions

Reaction Steps

Phenyl magnesium bromide (2.68 mL) in diethylether (3.0M) was added dropwise to 1.00 gram of dimethyl-2,5-dimethyl-4-chloromethyl-1,4-dihydropyridine-3,5-dicarboxylate 11a (3.66 mm) [See; e.g., E. Benary, Chem. Ber., 44, 489 (1911)] in dry tetrahydrofuran under an argon atmosphere at -78° C. Stirring was continued at -78° for 15 minutes followed by warming to -10° C. for 1 hour. The excess Grignard reagent was quenched with saturated aqueous ammonium chloride. Extraction with ethyl acetate (3×75 mL), washing the organic portion with saturated aqueous NaCl, drying (MgSO4), filtering, and evaporation gave crude product. Crystallization from toluene/hexane (1/1) gave 1.10 gr (92%) of pure dimethyl-4-phenyl-4,5-dihydro-2,7-dimethylazepine-3,6-dicarboxylate (11).

Provenance & Evidence