Ethanol → 3-Ethyl-4,6-dihydroxy-2-(methoxycarbonylmethyl)benzoic acid methyl ester

Participants

Reaction Steps

The above-obtained penta-2,3-dienedioic acid dimethyl ester (4.6 g, 30 mmol) and 1-ethoxy-1,3-bis(trimethylsiloxy)hexa-1,3-diene (13 g, 41 mmol) were mixed and stirred at a room temperature for 1.5 hours. The reaction mixture was added with ethanol (100 mL) and ammonium fluoride (5.4 g) and stirred at a room temperature for 2 hours. The reaction mixture was further added with water and extracted with ethyl acetate 3 times. The organic layers were combined, sequentially washed with water and saturated brine, dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was triturated with hexane (50 mL) to obtain Compound 23 (3.2 g, 40%).

Provenance & Evidence