Oxygen → (R)-2-bromo-octanoic acid

참여 물질

반응 단계

A catalyst solution was prepared by dissolving 0.035 g (0.0045 mmol) of Ru(OAc)2 [(R)-BIPHEMP] and 17.2 mg (0.0905 mmol) of an 85 percent ethereal HBF4 solution in 20 ml of methanol in a glove box (O2 content <1 ppm) and was stirred at 20° for 1.5 hours. Then, 1.0 g (4.52 mmol) of (Z)-2-bromo-2-octenoic acid and 105 ml of methanol were placed in a 185 ml autoclave and the above-prepared catalyst solution was added. The autoclave was sealed and the hydrogenation was carried out at 50° while stirring and under a constant pressure of 50 bar. After 21 hours the conversion was 98%. The hydrogenation solution was evaporated at 50°/20 mbar and the residue was distilled at 115°/0.2 mbar in a bulb tube oven. There was obtained 0.6 g of (R)-2-bromo-octanoic acid as a colourless oil; chem. purity 97.3 GC area%; 86.0% ee.

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