Sodium bis(trimethylsilyl)amide → HCID 58380065, compound

Participants

Reaction Steps

To 75 mL dry THF was added methyl 2-(benzyloxy)-5-(3-methoxy-3-oxopropyl)isonicotinate (2.50 g, 7.59 mmol). The temperature of the solution was lowered to −78° C. To this solution was added 1N sodium bis(trimethylsilyl)amide (15.2 mL, 15.2 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) dropwise over 30 minutes. After completion, the reaction was stirred for an hour and then quenched by addition of 25 mL saturated NH4Cl. The organic layer was extracted with EtOAc and washed with 150 mL water and 100 mL brine, and then dried over MgSO4. The organic solvent was evaporated, and the residue was purified by column chromatography with 15% EtOAc/hexane to give desired product H6.4 (1.90 g, 84.1%). MS ESI (pos.) m/e: 298.1 (M+H)+.

Provenance & Evidence