Acetone → (2R)-4-[(3-Chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)butanoic acid

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Reaction Steps

Following the general procedure of the oxidation of aldehydes to carboxylic acids of Description 13, (3R)-2,2-dimethyl-4-oxo-3-(1,1,2,2-tetramethyl-1-silapropoxy)butyl (3-chloropropyl)sulfonate (15b) (1.1 g, 2.8 mmol) dissolved in 20 mL of acetone was reacted with 1.4 mL of Jones-reagent (2.0 M in water). After work-up, 0.9 g (79% yield) of the title compound (15) was obtained as a colorless oil. 1H NMR (400 MHz, CDCl3): δ=0.13 (s, 3H), 0.16 (s, 3H), 0.98 (s, 9H), 1.05 (s, 3H), 1.11 (s, 3H), 2.32-2.39 (m, 2H), 3.33-3.36 (m, 2H), 3.69-3.72 (m, 2H), 4.04 (d, J=9.6 Hz, 1H), 4.09 (s, 1H), 4.12 (d, J=9.6 Hz, 1H) ppm. MS (ESI) m/z 403.00 (M+H)+; 401.05 (M−H)−. The analytical data was consistent with the proposed structure.

Provenance & Evidence