Benzyl Bromide → HCID 86731480, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-ethoxy-4-oxocyclohexanecarboxylic acid (0.777 g, 4.17 mmol) in DMF (15 mL) was added potassium carbonate (1.153 g, 8.35 mmol) followed by benzyl bromide (0.546 mL, 4.59 mmol). The mixture was heated at 60° C. for 18 h, then cooled to rt. The mixture was diluted with water (30 mL) and extracted with ethyl acetate (2×30 mL). The organic layers were washed with water (3×30 mL), then with brine and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography using a 0-25% ethyl acetate in hexanes gradient and a 24 g silica gel column to give benzyl 1-ethoxy-4-oxocyclohexanecarboxylate (0.9 g, 3.26 mmol, 78% yield) as a light-yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.40-7.32 (m, 5H), 5.21 (s, 2H), 3.48 (q, J=6.9 Hz, 2H), 2.65-2.54 (m, 2H), 2.39-2.27 (m, 4H), 2.20-2.09 (m, 2H), 1.24 (t, J=7.0 Hz, 3H).

Provenance & Evidence