Potassium chromate(VI) → HCID 59557758, compound

Participants

Reaction Steps

To a stirred solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (10 g, 10.8 mmol) in acetic acid (130 mL) at 120° C. was added potassium chromate (6.3 g, 21.4 mmol) in one portion. The mixture was stirred for 22 hours at this temperature, and the reaction was cooled to RT. The volatiles were removed under reduced pressure, ethyl acetate was added, and the solids were filtered off. The organic layer was washed with a saturated solution of sodium bicarbonate and then with brine, and dried over sodium sulfate. Concentration of the organic solution and purification of the resulting residue by silica gel column (3:1 petroleum ether:ethyl acetate) gave 2.3 g of title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.90 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.4 Hz, 1H), 7.26 (d, J=8.4 Hz, 2H), 7.22 (dd, J=8.4, 2.2 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H), 5.31 (t, J=9.4 Hz, 1H), 5.22 (t, J=9.8 Hz, 1H), 5.09 (t, J=9.4 Hz, 1H), 4.35 (d, J=10.0 Hz, 1H), 4.29 (dd, J=12.4, 4.8 Hz, 1H), 4.18-4.13 (m, 3H), 3.85-3.81 (m, 1H), 2.60 (s, 3H), 2.09 (s, 3H), 2.07 (s, 3H), 2.01 (s, 3H), 1.75 (s, 3H); MS ESI (m/z): 575 [M+H]+, 619 [M+HCO2]−.

Provenance & Evidence