Sodium hydride → HCID 86617111, compound

Participants

Reaction Steps

To a solution of the product from Step 6 (22.0 g, 52.8 mmol) in N,N-dimethylformamide (220 mL) was added sodium hydride (60% suspension in mineral oil, 3.38 g, 84.6 mmol) in several portions. The reaction was stirred at room temperature for 16 hours and then ice water (50 mL) was added slowly. The resulting mixture was partitioned between ethyl acetate and H2O and the organic phase washed with 2% aqueous lithium chloride solution and then brine. The organic layer was dried over sodium sulfate and concentrated to an oil that was separated by silica gel chromatography (75M Biotage Si1 (A Dynax Corp.; Charlottesville, Va.) eluting with a pentane/EtOAc gradient (4:1-1:1) to afford 17.7 g (53%) of the product as a solid. MS m/z 336.3 (AP+100).

Provenance & Evidence