1-Bromo-2-methylpropane → HCID 68603776, compound

Participants

Reaction Conditions

Reaction Steps

A separated flask was charged with 1-(2-(2-methoxyethoxy)phenyl)ethanone (11.2 g, 57 mmol). (1-(2-(2-Methoxyethoxy)phenyl)ethanone was prepared by a procedure analogous to Example 1, in which commercially 1-bromo-2-methoxyethane was substituted for 1-bromo-2-methyl propane). The 1-bromo-2-methoxyethane was added to anhydrous THF (50 mL) and cooled to −78° C. To this solution was added commercially available lithium hexamethyl-silylamide (1M in hexanes, 172 mL, 172 mmol, Aldrich) over a 3 hour period at −78° C. The mixture was stirred for an additional 2 hours at −78° C. To the resulting mixture were added dropwise a solution of CDI and 4-acetamido-3-ethylbenzoic acid (above) at −78° C. The resulting mixture was stirred at −78° C. for an additional 30 min and subsequently allowed to warm up to room temperature over 12 h. The reaction was quenched with 1 N HCl and extracted with EtOAc and water. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography to give 1-(4-acetamido-3-ethylphenyl)-3-(2-(2-methoxyethoxy)phenyl)propane-1,3-dione as a white solid (11 g, 60%).

Provenance & Evidence