Triacetoxyperiodinane → HCID 86705541, compound

Participants

Reaction Steps

To a stirred solution of 326 (1.134 g, 3.914 mmol) and DCM (8 mL) under nitrogen cooled to 0° C. was added NaHCO3 (0.9864 g, 11.74 mmol) followed by Dess-Martin periodinane (2.490 g, 5.871 mmol) both as solids. After 3 h, the reaction was about 50% complete by TLC. The reaction was warmed to RT for 1 h, then the reaction was diluted with Et2O (10 mL) and poured into ice cold satd. aq. NaHCO3 (50 mL) containing sodium bisulfite (15 gm). After stirring for 15 min, the layers were separated and the aqueous phase was extracted with Et2O (2×30 mL). The combined organic extracts were washed sequentially with satd. aq. NaHCO3 (2×50 mL) and brine (1×50 mL), dried (MgSO4), filtered and concentrated to afford 0.814 g (72%) of (S)-tert-butyl 1-(3-chloro-4-fluorophenyl)-2-oxoethylcarbamate (328) as a yellow foam.

Provenance & Evidence