Ethyl formate → 2-Cyclopentyl-6-hydroxymethylene-3-methoxy-cyclohex-2-enone

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Reaction Steps

To a suspension of sodium hydride (2.04 g, 60% suspension, 51 mmol) in benzene (100 mL), a mixture of ethyl formate (6.7 g) and 2-cyclopentyl-3-methoxycyclohex-3-en-1-one (2.82 g, 17 mmol) in benzene was added dropwise at 5° C. The reaction mixture was stirred at ice temperature for 1 hour and 18 hours at room temperature. The reaction mixture was cooled in ice bath, and 200 mL of 10% sodium hydrogen phosphate solution was added dropwise. The organic layer was separated, and aqueous layer was extracted with ethyl acetate (2×50 mL). Combined organic extract was washed with brine and dried over anhydrous sodium sulfate. Solvent was removed in vacuo and the resulting product was purified on a column of silica gel (Hex:EtOAc) to give the title compound as a viscous liquid (2 g, 60%).

Provenance & Evidence