Methyl acetoacetate → 5-Methyl-1-phenylhexan-1-one

Participants

Reaction Steps

The title compound was prepared as described in General Method 1 using 14.2 mmol of methyl acetoacetate, 15.6 mmol of NaH 60% dispersion in oil, 14.9 mmol of 1.6 M n-butyl lithium in hexane, 14.2 mmol of isoheptanophenone and 50 mL of tetrahydrofuran. Isoheptanophenone was prepared by reacting the appropriate acid chloride with AlCl3 in benzene as described by Vogel in Practical Organic Chemistry 1978, 770-775. Upon concentrating the reaction, a solid precipitated out which was recrystallized from ethyl acetate (m.p. 124-125° C.). 1H NMR (CDCl3) δ 0.80 (d,d, 6 H), 1.1-1.2 (m, 2 H), 1.15-1.40 (m, 2 H), 1.4-1.5 (m, 1 H), 1.9-2.0 (m, 2 H), 2.88 (d, 1 H), 2.9 (d, 1 H), 3.2 (d, 1 H), 3.3 (d, 1 H), 7.2-7.5 (m, 5 H).

Provenance & Evidence