Ethanol → Ethyl 4-[3-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-oxo-propenyl]-benzoate

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Reaction Steps

Methyl 4-formylbenzoate (185 mg, 1.13 mmol) was added to a solution of 1-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound 11, 293 mg, 1.13 mmol) in 5 mL of 1 N NaOH and 10 mL of methanol. After stirring at room temperature for 18 h, the reaction mixture was 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. The residue was then added to a solution of ethanol (520 mg, 11.30 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (433 mg, 2.26 mmol) and N,N-dimethylaminopyridine (DMAP) (13 mg, 0.11 mmol) in 5 mL of dichloromethane. After stirring at room temperature for 8 h, water (10 mL) was added and the mixture was extracted with ethyl acetate (3×5 mL), washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (80:20 hexane/ethyl acetate) afforded the title compound (153 mg, 32% yield) as a colorless oil:

Provenance & Evidence