반응 #444988

반응 방정식

4-chlorobenzaldehyde

NaH

n-butyl lithium

methyl acetoacetate

→

title compound

6-(4-Chlorophenyl)-5,6-dihydro-4-hydroxy-2H-pyran-2-one

용매

hexane

tetrahydrofuran

반응 조건

후처리

1. 1
   기타The crude product was triturated from diethyl ether

실험 절차

The title compound was prepared as described in General Method 1 using 10 mL of methyl acetoacetate, 3.9 g of NaH 60% dispersion in oil, 58 mL of 1.6M n-butyl lithium in hexane, 13.5 g of 4-chlorobenzaldehyde and 250 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 15 minutes at 0°0 C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 149°-150° C.). 1H NMR (CDCl3) δ 2.83 (dd, 1 H), 2.95 (dd, 1 H), 3.60 (dd, 2 H), 5.67 (dd, 1 H), 7.33-7.44 (m, 4 H).

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