(R)-3-hydroxymethylheptanoic acid, (S)-1-phenylethylamide → (R)-4-butyldihydrofuran-2-one

Participants

Reaction Steps

(R)-3-Hydroxymethylheptanoic acid, (S)-1-phenylethylamide (8.4 g, 31.9 mmol) was dissolved in 1 M H2SO4/dioxane (1:1, 110 mL) and the resulting solution was refluxed overnight under argon. After cooling to rt, the reaction mixture was diluted with ethyl acetate/hexanes (1:3, 200 mL) and washed with water (2×100 mL), saturated aq. NaHCO3 (2×100 mL), and brine (100 mL). The solution was dried (Na2SO4), filtered, and concentrated to afford pure (R)-4-butyldihydrofuran-2-one as a colorless oil (3.5 g, 78%).

Provenance & Evidence