Sodium hydride → HCID 23352258, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of sodiumhydride (3.6 g, 90mmol) and N,N-dimethylformamide (150 ml) was cooled to 0° C. and treated with solid di-tert-butyliminodicarboxylate (17.4 g, 76.0 mmol) with vigorous stirring. The mixture was stirred at 0° C. for 15 minutes, the ice bath was removed and a solution of methyl 3,5-bis(bromomethyl)-benzoate (23.6 g, 73.2 mmol) in N,N-dimethylform was added dropwise over 30 minutes. After 12 hours the mixture was poured into 100 ml 1/4 saturated aqueous ammonium chloride and extracted with the three 100 ml portion of hexanes. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure and chromatographed using a gradient of 10-20% ethyl acetate/hexanes to yield the product (22.0 g, 66% yield). TLC (20% ethyl acetate/hexanes): Rf =0.55 (UV active, CAM stain)

Provenance & Evidence