Potassium Hydroxide → 2-[(E)-2-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propenyl]-3H-imidazole-4-carboxylic acid

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Reaction Conditions

Reaction Steps

Ethyl (E)-2-[2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalen-2-yl)propen-1-yl]-5imidazolecarboxylate (Compound 5, 0.043 g, 0.153 mmol) was dissolved in ethanol (2 mL) and treated with 2N aqueous KOH (0.5 mL). The solution was stirred for 20 hours at 50° C. and concentrated under vacuum. The residue was treated with ether (10 mL) and water (1 mL) and neutralized with saturated aqueous NH4Cl. The layers were separated and the aqueous layer extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was passed through a small plug of silica gel (methanol) to give the title compound as a pale yellow powder (40 mg, 80%).

Provenance & Evidence