反应详情

Following the general procedure for the oxidation of aldehydes to carboxylic acids of Description 13, (3R)-2,2-dimethyl-4-oxo-3-(phenylmethoxy)butyl (3-chloropropyl)sulfonate (11b) (10.0 g, 27.5 mmol) dissolved in 200 mL of acetone was reacted with 13.7 mL of Jones-reagent (2.0 M in water). After work-up, 10.0 g (96% yield) of the title compound (11) was obtained as a colorless oil. 1H NMR (400 MHz, CDCl3): δ=1.11 (s, 3H), 1.13 (s, 3H), 2.27-2.34 (m, 2H), 3.26-3.29 (m, 2H), 3.65-3.68 (m, 2H), 3.91 (s, 1H), 4.04 (d, J=9.6 Hz, 1H), 4.21 (d, J=9.6 Hz, 1H), 4.50 (d, J=10.8 Hz, 1H), 4.69 (d, J=10.8 Hz, 1H), 7.33-7.38 (m, 5H) ppm. 1H NMR (400 MHz, DMSO-d6): δ=0.97 (s, 3H), 1.01 (s, 3H), 2.07-2.16 (m, 2H), 3.41-3.46 (m, 2H), 3.69-3.73 (m, 2H), 3.76 (s, 1H), 3.99 (d, J=9.6 Hz, 1H), 4.14 (d, J=9.2 Hz, 1H), 4.35 (d, J=11.2 Hz, 1H), 4.53 (d, J=11.2 Hz, 1H), 7.27-7.37 (m, 5H), 12.05 (v. br., s, 1H) ppm. MS (ESI) m/z 379.12 (M+H)+, 401.02 (M+Na)+, 376.9 (M−H)−. The analytical data was consistent with the proposed structure.

1. customwas reacted with 13.7 mL of Jones-reagent (2.0 M in water)