Methyl acetoacetate → HCID 54721634, compound

Participants

Reaction Steps

The title compound was prepared as described in General Method 1 using 5.6 mmol of methyl acetoacetate, 6.1 mmol of NaH 60% dispersion in oil, 5.9 mmol of 1.6M n-butyl lithium in hexane, 5.6 mmol of 5-oxo-5-phenylpentanoic acid benzylmethyl amide and 25 mL of tetrahydrofuran. The product was flash chromatographed using CH2 Cl2 /MeOH (98/2) to give a solid (m.p. 47°-51° C.). 1H NMR (DMSO-d6) δ1.1-1.3 (m, 1H), 1.4-1.6 (m, 1H), 1.8-2.0 (m, 2H), 2.2-2.4 (m, 2H), 2.75/2.81 (s/s 3H), 2.85-3.1 (m, 2H), 4.4/4.5 (s/s, 2H), 4.85/4.9 (s/s 1H), 7.1-7.4 (m, 10H), 11.36/11.38 (s/s, 1H).

Provenance & Evidence