Methyl acetoacetate → HCID 54682304, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared as described in General Method 5 using 2.56 g (22 mmol) of methyl acetoacetate, 0.97 g (24.2 mmol) of NaH 60% dispersion in oil, 14.4 mL (23.1 mmol) of 1.6 M n-butyl lithium in hexane, 4.5 g (22.0 mmol) of 6-methyl-1-phenyl-heptan-3-one (A. Katritzky, et al., J. Org. Chem., 1995, 60 (23), 7605) and 60 mL of THF. After addition of the ketone, the reaction was stirred for 90 minutes at 0° C. and then for 30 minutes at room temperature. Water (400 mL) was slowly added with vigorous stirring, and the reaction was allowed to stir overnight. The reaction was worked up as in General Method 6. The product was triturated from ether to afford a solid, m.p. 99-100.5° C. 1H NMR (CDCl3) δ 0.89-0.92 (d,d, 6 H), 1.24-1.32 (m, 2 H), 1.48-1.57 (m, 1 H), 1.64-1.83 (m, 2 H), 1.94-2.03 (m, 2 H), 2.68-2.77 (m, s, 4 H), 3.42 (s, 2 H), 7.16-7.32 (m, 5 H).

Provenance & Evidence