Methyl acetoacetate → HCID 54682293, compound

Participants

Reaction Steps

The title compound was prepared as described in General Methods 6 and 7 using 2.4 mL (22.2 mmol) of methyl acetoacetate, 1.02 g (25.5 mmol) of 60% sodium hydride, 16 mL (25.6 mmol) of 1.6 M n-butyllithium, 6.2 g (18.2 mmol) of 3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-phenyl-propan-1-one from Example Q and 180 mL of THF. After standard work-up, the crude aldol product was dissolved in THF (60 mL), treated with 0.2N NaOH (500 mL), and stirred at room temperature. The title compound was isolated via the normal procedure. 1H NMR (CDCl3) δ 2.21 (m, 2 H), 2.38 (m, 1 H), 2.61 (m, 1 H), 2.93 (dd, 2 H), 3.28 (dd, 2 H), 6.54-6.65 (m, 3 H), 7.06 (m, 1 H), 7.28-7.40 (m, 6 H).

Provenance & Evidence