Ethanol → HCID 18942524, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,3-dimethyldihydrofuran-2(3H)-one (1 eq.) in ethanol (1 M) was added 8 N KOH (17 eq.). The mixture was stirred overnight, and the ethanolic solvent was concentrated in vacuo. To the remaining aqueous solution was added ethyl acetate and cooled to −15° C. Concentrated HCl was added dropwise until pH<1, taking care the internal temperature does not exceed 10° C. The aqueous layer was extracted with ethyl acetate three times. The combined organic extracts were dried over anhydrous Na2SO4, filtered, and cooled in an ice water bath. A solution of diazomethane in ether was added until a yellow color persisted. The reaction was stirred for an additional 10 min at rt and then concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 10 to 60% EtOAc in Hex) to afford the title compound as an oil.

Provenance & Evidence