Sodium Hydroxide → [4-(3-Phenyl-1,7-naphthyridin-2-yl)phenyl]methanol

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Reaction Conditions

Reaction Steps

To a partial suspension of 1-[4-({[t-butyl-(dimethyl)silyl]oxy}methyl)phenyl]-2-phenylethanone (1.03 gm, 3.0 mmol) and N-formyl-N-(4-formylpyridine-3-yl)-2,2-dimethylpropanamide (704 mg, 3.0 mmol) in absolute ethanol (8 mL) was added dropwise 5N NaOH (2.5 mL, 12.5 mmol). This mixture was heated at 70° C. over night. The solvent was evaporated in vacuo and the residue was partitioned between methylene chloride and aqueous sodium carbonate. The organic layer was dried (Na2SO4), the solution filtered, and the solvent evaporated. This residue was chromatographed on a column of silica gel eluting with 40-100% ethyl acetate/hexane and then 0.5-1.5% methanol/ethyl acetate (sat'd with ammonia). The appropriate fractions were combined and the solvents evaporated. The residue was triturated with diethyl ether to give crystalline title compound. 1H-NMR (500 MHz, CDCl3): δ 9.60 (1H, s), 8.65 (1H, d, J=5.5 Hz), 8.17 (1H, s), 7.71 (1H, d, J=5.6 Hz), 7.48 (2H, d, J=6.5 Hz), 7.25-7.36 (7H, m), 4.72 (2H, s). m/e (m+1): 313.2.

Provenance & Evidence