Sodium hydride → HCID 67953937, compound

Participants

Reaction Steps

A solution of compound 6-C (0.70 g, 2.64 mmol) in DMF (20 mL) was cooled in an ice bath and treated with a 60% dispersion of NaH in mineral oil (0.126 g, 3.17 mmol) and stirred at ambient temp for 30 min. The solution was cooled on an ice bath and treated with methyl 4-(chlorosulfonyl)benzoate (1.24 g, added in portions). The resultant solution was stirred at ambient temperature for 18 hours. The solution was poured into ice water, and the resultant suspension was made basic with careful addition of a saturated aqueous solution of NaHCO3. The solid was collected by filtration, washed with water and air dried. The solid was pre-absorbed onto silica gel and purified by flash chromatography, using a gradient of EtOAc (10-60%) in heptanes as the eluant to afford compound 6-D as a colorless solid (1.1 g, 90%). MS: m/z 464.1 (MH+).

Provenance & Evidence