Sodium Hydroxide → HCID 90386740, compound

Participants

Reaction Steps

Oxalyl dichloride (0.053 mL, 0.625 mmol) was added dropwise to N,N-dimethylformamide (0.387 mL, 5 mmol) at 0° C. The reaction mixture was removed from the cooling bath and stirred for thirty minutes at ambient temperature. N,N-Dimethylformamide (1 mL) was added to the reaction mixture and stirring was continued for another 30 minutes. The mixture was again cooled to 0° C. and a solution of Example 72b (0.161 g, 0.5 mmol) in N,N-dimethylformamide (2 mL) was added. Stirring was continued at 0° C. for two hours and then at ambient temperature for 3.5 hours. A solution of sodium hydroxide (10 mL, 4 N aqueous) was added and the mixture was stirred for 20 minutes. The reaction mixture was then partitioned between ethyl acetate and water, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 5-50% ethyl acetate in hexanes) to give 0.16 g (92%) of the title compound.

Provenance & Evidence