Oxolane--water (1/1) → 4-(4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

Participants

Reaction Steps

Dissolve 4-Benzyl-3-[2-(4-benzyloxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one (3.09 g, 5.89 mmol) in 3/1 mix of THF/water (100 ml). Add OsO4 (5.99 g, 0.59 mmol) and NaIO4 (3.82 g, 17.86 mmol). Stir the resulting suspension for 3 hr at room temperature. Quench with 1M solution of sodium thiosulfate (300 ml). Extract in ethyl acetate. Column separation affords 0.885 g (28.5%) of 4-(4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde.

Provenance & Evidence