Methyl acetoacetate → 4-Hydroxy-6-(4-methoxyphenyl)-5,6-dihydro-2H-pyran-2-one

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared as described in General Method 1 using 5 mL of methyl acetoacetate, 2.0 g of NaH 60% dispersion in oil, 25 mL of 2.0M n-butyl lithium in hexane, 7.0 mL of 4-methoxybenzaldehyde and 150 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 15 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.159°-162° C. (dec.)). 1H NMR (CDCl3) δ 2.91 (dd, 2 H), 3.57 (dd, 2 H), 3.83 (s, 3 H), 5.66 (dd, 1 H), 6.93-6.97 (m, 2 H), 7.30-7.34 (m, 2 H).

Provenance & Evidence