Phosphate → HCID 14486197, compound

Participants

Reaction Conditions

Reaction Steps

Phosphate buffer (pH 7, 680 ml), potassium permanganate (0.98 g, 0.006 mole), sodium periodate (87.3 g, 0.41 mole) and acetone (320 ml) were combined at ambient temperature and then cooled to 0° C. Over 8 minutes unsaturated ester of Example 1 (33.6 g, 0.08 mole) in acetone (320 ml) was added. The reaction was stirred 30 minutes at 0°-5° C. and then allowed to warm to ambient temperature. Over 1 hour reaction time the purple solution had changed to a pink color, and 30 ml of aqueous potassium permanganate (15 g, 0.095 mole in 500 ml water) was added. At 1 hour intervals, two more portions (50 ml and 75 ml) of aqueous potassium permanganate were added. The reaction was complete after 6 hours. Water (500 ml) and ethyl acetate were added, and the phases separated. The aqueous phase was extracted with ethyl acetate (3×250 ml). The combined organic layers were washed with water (2×500 ml), dried with sodium sulfate, and solvent removed under vacuum yielding 22.7 g (92%) of a thick colorless oil. Crystals formed on standing at 0° C.; m.p. 101°-102° C. IR(CHCl3) 3404, 2950, 2930, 2886, 2856, 1793, 1463, 1321, 1145, 1128 cm-1. NMR(250 MHz) 6.53 (bs, 1H), 4.74 (d, J=2.1 Hz, 1H), 4.32 (m, 1H), 3.56 (t, J=2.5 Hz, 1H), 2.96 (s, 3H), 1.26 (d, J=6 Hz, 3H), 0.86 (s, 9H), 0.07 (s, 3H), 0.05 (s, 3H).

Provenance & Evidence