Sulfuric acid magnesium salt (1:1) → HCID 19834297, compound

Participants

Reaction Steps

A mixture of 19.2 grams (69.6 mmol) of 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 0.8 grams of 10% palladium on carbon, 2.0 grams of anhydrous magnesium sulfate and 100 ml of anhydrous tetrahydrofuran is hydrogenated (48 psi, 25° C.) on a Parr apparatus for three hours. Solids are then removed by filtration. To the filtrate are added 19.7 grams (58.0 mmol) of 1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl acrylate, 0.8 gram of potassium tert-butoxide and 40 ml of tetrahydrofuran. The reaction mixture is purged with nitrogen, stoppered and allowed to stand at 25° C. for five days. The mixture is then diluted with diethyl ether (200 ml), and washed successively with 1N hydrochloric acid (2×75 ml) and saturated sodium bicarbonate solution (200) ml), and then dried over anhydrous magnesium sulfate and concentrated to a pink residue. Purification by flash chromatography on silica gel (4:1, heptane:ethyl acetate) affords 12.7 grams (35% yield) of the title compound as a colorless syrup.

Provenance & Evidence