Acetic Acid → HCID 11270256, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 11 (20.0 g, 52 mmol) and malonic acid (8.10 g, 100 mmol) was added, sequentially, CH3CN (100 mL), pyridine (2.1 mL, 30 mmol) and morpholine (0.09 mL, 1.0 mmol). The mixture was then heated to reflux and the solvent distilled. The volume of the reaction was maintained constant by addition of fresh CH3CN until ˜30 volumes of solvent were distilled. The reaction was then cooled to 5° C. and a solution of acetic acid (2.08 mL, 36 mmol) in CH3CN (20 mL) added. The precipitated solid was filtered, washed with cold CH3CN (40 mmol) and H2O (40 mL) then slurried overnight in heptane (150 mL) at 35° C. The solid was filtered, rinsed with heptane (40 mL) and dried overnight in vacuo to yield 17.8 g (80%) of the title compound 7 as a white solid. 1HNMR (DMSO-d6): δ 0.26 (s, 6H), 0.83 (t, J=7.5 Hz, 3H), 0.94 (s, 9H), 2.35 (q, J=7.5 Hz, 2H), 6.39 (d, J=8.4 Hz, 2H), 6.53 (d, J=16 Hz, 1H), 6.58 (d, J=8.4 Hz, 2H), 7.06-7.18 (m, 5H), 7.2 (d, J=8 Hz, 2H), 7.59 (d, J=16 Hz, 1H), 7.69 (d, J=8 Hz, 2H), 9.19 (s, 1H); MS, m/z 485 (M+H)+.

Provenance & Evidence