Tetrahydrofuran → N-[3,5-dibromo-4-[3-formyl-4-hydroxy-5-isopropylphenoxy]-2-methyl-phenyl]malonamic acid ethyl ester

Participants

Reaction Steps

To a stirred solution of ethyl malonylchloride (7.2 μl, 0.056 mmol) and compound 5-(4-amino-2,6-dibromo-3-methylphenoxy)-2-hydroxy-3-isopropylbenzaldehyde of Part 8E (25 mg, 0.056 mmol) in THF (0.5 mL) was added Et3N (15.7 μl, 0.112 mmol) at 4° C. After 30 minutes stirring at room temperature, the reaction mixture was washed with NH4Cl (saturated aqueous solution) and the organic phase removed in vacuo. The water phase was extracted with CHC13 and the two phases were separated with a phase separator (IST). The organic phase was concentrated and the resulting residue was purified on column (silica gel, gradient elution: n-heptane/EtOAc from 1:0 to 7:3) to give 15 mg (48%) of N-[3,5-dibromo-4-[3-formyl-4-hydroxy-5-isopropylphenoxy]-2-methylphenyl]-malonamic acid ethyl ester as a light yellow residue.

Provenance & Evidence