Triacetoxyperiodinane → HCID 86705754, compound

Participants

Reaction Steps

4-(5,6-Dichloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)butan-1-ol (1.008 g, 2.59 mmol) was dissolved in DCM (35 ml) and Dess-Martin reagent (1.208 g, 2.85 mmol) was added at r.t. under N2. The reaction was left for 2 hrs. The reaction was quenched by the addition of 1M Na2S2O3 solution (10 ml), sat. NaHCO3 solution (40 ml) and DCM (80 ml). The organic layer was separated and the aqueous layer was extracted with DCM (3×80 ml). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 15% EtOAc:85% heptanes and 100% EtOAc as eluent to give the product as a pale yellow oil (0.595 g, 59%): MS (ESI+) for C17H24Cl2N2O2Si m/z 388.4 [M+H]+; LC purity 91% (ret. time, 1.74 min); 1H NMR (500 MHz, CDCl3) δ 9.82 (s, 1H), 7.79 (s, 1H), 7.53 (s, 1H), 5.44 (s, 2H), 3.43-3.67 (m, 2H), 2.97 (t, J=7.49 Hz, 2H), 2.69 (t, J=7.25 Hz, 2H), 2.23 (quin, J=7.13 Hz, 2H), 0.78-1.02 (m, 2H), −0.02 (s, 9H).

Provenance & Evidence