Ethyl Acetoacetate → 6-[1,1'-Biphenyl]-4-yl-6-butyl-5,6-dihydro-4-hydroxy-2H-pyran-2-one

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared as described in General Method 1 using 13 g ethyl acetoacetate, 5.3 g of NaH 60% dispersion in oil, 60 mL of 1.6M n-butyl lithium in hexane, 21 g of 1-[1,1'-biphenyl]-4-yl-1-pentanone and 300 mL of tetrahydrofuran. After addition of the ketone, the reaction was stirred 15 minutes at -78° C. and 2 hours at room temperature. The crude reaction mixture afforded a solid which was washed with CH2 Cl2 and two times with ethyl acetate (m.p. 165°-170° C). 1H NMR(d6 -DMSO) δ 0.7-1.9 (m, 7 H), 2.0 (m, 2 H), 3.0 (s, 2 H), 4.9 (s, 1 H), 7.3-7.8 (m, 9 H), 11.3 (s, 1 H).

Provenance & Evidence