Potassium Carbonate → HCID 22324896, compound

Participants

Reaction Steps

A mixture of 6-hydroxy-5-(2-phenylethyl)-3,4-dihydro-1(2H)-naphthalenone (2.00 g, 7.5 mmol), potassium carbonate (2.08 g, 15.0 mmol), and acetonitrile (15 mL) was heated to reflux, whereupon ethyl 2-bromo-2-methylpropanoate (1.2 mL, 8.3 mmol) was added. The mixture was stirred at reflux for 2.5 h, whereupon further potassium carbonate (1.04 g, 7.5 mmol) and ethyl 2-bromo-2-methylpropanoate (1.2 mL, 8.3 mmol) were added. The mixture was stirred at reflux for a further 22 h and was then filtered and concentrated. The residue was purified by dry-flash column chromatography (SiO2, 5-30% ethyl acetate-hexane) to give ethyl 2-methyl-2-{[5-oxo-1-(2-phenylethyl)-5,6,7,8-tetrahydro-2-naphthalenyl]oxy}propanoate as a pale yellow oil, 2.75 g, 96% yield. NMR spectrum was consistent with structure. MS EI: M+• 380.1985 (M+• 380.1988). 2. 6-(2-Hydroxy-1,1-dimethylethoxy)-5-(2-phenylethyl)-1,2,3,4-tetrahydro-1-naphthalenol

Provenance & Evidence