Ethyl formate → 6-Hydroxymethylene-2-isopropyl-3-methoxy-cyclohex-2-enone

Participants

Reaction Steps

To a suspension of sodium hydride (3.6 g, 60% suspension, 90 mmol) in benzene (100 mL), a mixture of ethyl formate (12.5 g) and 2-isopropyl-3-methoxy-cyclohex-2-enone (5g, 29.7 mmol) in benzene was added dropwise at 5° C. The reaction mixture was stirred at ice temperature for 1 hour, and at room temperature for 18 hours. The reaction mixture was cooled in an ice bath, and 10% sodium hydrogen phosphate solution (200 mL) was added dropwise. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. The 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 thick viscous liquid (3.5 g, 60%). 1H NMR (CDCl3): δ 1.15 (d, 6H, 2×CH3), 2.35–2.6 (m, 4H, 2×CH2), 3.15 (m, 1H, CH), 3.8 (s, 3H, OCH3), 7.17 (d, 1H, ═CHOH).

Provenance & Evidence