2-Methoxynaphthalene → HCID 67674172, compound

Participants

Reaction Conditions

Reaction Steps

Aluminium chloride (2,49 g, 18,7 mmol) was added in 2 portions to a solution of 2-methoxynaphthalene (1,97 g, 12,5 mmol) in dichloromethane (15 mL) at 5° C. The red solution was cooled to -20° C. and the reaction vessel was evacuated to a pressure of 160 mbar. Ethyl pyruvate (2,17 g, 18,7 mmol) in dichloromethane (pre-cooled, 5 mL) was added over 5 minutes and the temperature was further reduced to -40° C. The reaction was allowed to proceed for 2 hours, at which time the system was opened to the atmosphere and poured on to ice. Ethyl 2-hydroxy-2-(6-methoxynaphth-6-yl)propionate was formed with a selectivity of 35% at 62% conversion of the starting material.

Provenance & Evidence