Hydrochloric Acid → 2-Trimethylsilanyl-ethyl 4-[3-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-naphthalen-2-yl)-3-oxo-propenyl]-benzoate

Participants

Reaction Steps

Methyl 4-formylbenzoate (available from Aldrich, 113 mg, 0.69 mmol) was added to a solution of 1-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-naphthalen-2-yl)-ethanone (Compound 5, 200 mg, 0.69 mmol) in 10 mL of 1 N NaOH and 20 mL of methanol. After stirring at room temperature for 18 h, the reaction mixture was acidified with 1N HCl and extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure to give a yellow crude solid. This crude solid was then dissolved in 10 mL of dichloromethane and 1 mL of trimethylsilylethanol at 0° C. 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (EDCI) (265 mg, 1.38 mmol) and 4-dimethylaminopyridine (DMAP) (6 mg, 0.07 mmol) were added. After stirring at room temperature for 18 h, the reaction was quenched with water (10 mL), extracted with dichloromethane (3×10 mL), washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (90:10 hexane/ethyl acetate) yielded the title compound (155 mg, 43% yield) as a yellow oil:

Provenance & Evidence