反应详情

温度

0 °C

The title compound was prepared as described in the General Method 1 using 5 mmol of methyl acetoacetate, 5.5 mmol of NaH 60% dispersion in oil, 5.5 mmol of 1.6M n-butyl lithium in hexane, 5.5 mmol of butyrophenone and 14 mL of tetrahydrofuran. After addition of the ketone, the reaction was stirred for 90 minutes at 0° C. The reaction was poured into saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated, and the residue flash chromatographed using hexane/ethyl acetate 80/20 as eluent. The aldol product was stirred at room temperature in 100 mL of 0.1N NaOH for 3.5 hours. The reaction was worked up as in General Method 1 and the product triturated from diethyl ether to afford a solid (m.p. 131.5°-132° C.). 1H NMR (CDCl3) δ 0.88 (t, 3 H), 1.1-1.4 (m, 2 H), 1.95 (m, 2 H), 2.90 (d, 1 H), 2.92 (d, 1 H), 3.25 (d, 1 H), 3.35 (d, 1 H), 7.2-7.4 (m, 5 H).

1. extractionextracted with ethyl acetate
2. dry with materialThe organic layer was dried over MgSO4
3. concentrationconcentrated
4. customthe residue flash chromatographed
5. stirringThe aldol product was stirred at room temperature in 100 mL of 0.1N NaOH for 3.5 hours
6. customthe product triturated from diethyl ether