Methyl acetoacetate → 6-Butyl-5,6-dihydro-4-hydroxy-6-phenyl-2H-pyran-2-one

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared as described in General Method 1 using 2.7 mL of methyl acetoacetate, 1.1 g of NaH 60% dispersion in oil, 12.5 mL of 2.0M n-butyl lithium in hexane, 5.1 mL of valerophenone and 125 mL of tetrahydrofuran. After addition of the ketone, the reaction was stirred for 10 minutes at 0° C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 124°-126° C.). 1H NMR (CDCl3) δ 0.85 (t, 3 H), 1.28 (m, 4 H), 1.97 (m, 2 H), 2.90 (dd, 2 H), 3.30 (dd, 2 H), 7.28-7.42 (m, 5 H).

Provenance & Evidence