Ethyl 2-methylacetoacetate → HCID 86587764, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-amino-2,6-dimethyl-phenoxy)-2-isopropyl-phenol (136 mg, 0.50 mmol) in a mixture of ethanol (2 mL) and hydrochloric acid (12M, 0.17 mL) at 0° C. was added slowly a solution of sodium nitrite (45 mg, 0.65 mmol) in water (0.5 mL). After stirring at 0° C. for 30 minutes, the diazonium solution was added dropwise into a solution of ethyl-2-methyl acetoacetate (87 mg, 0.60 mmol) in ethanol (1 mL) and 1N sodium hydroxide (2.26 mL) at 0° C. The resulting mixture was warmed to room temperature, stirred for 1 hour, then diluted with water (10 mL) and 1M hydrochloric acid (1 mL), and extracted with ethyl acetate (15 mL). The organic layer was separated, washed with 1M hydrochloric acid (15 mL), brine (15 mL), dried (Na2SO4), filtered, and concentrated to give the title compound (193 mg) which was used in the next step without further purification. MS (APCI−) Calc: 384.2, Found: 383.3 (M−1).

Provenance & Evidence