Sodium Chlorite → HCID 90303344, compound

Participants

Reaction Conditions

Reaction Steps

A soln. of (2-(triisopropylsilyl)-5,6-dihydrofuro[2,3-d]thiazol-6-yl)methanol (1.77 g, 5.64 mmol)) in DCM (56 mL) was treated at 0° C. with DMP (2.87 g, 6.77 mmol) portionwise over 1 h. The mixture was stirred at 0° C. for 2 h, then, it was allowed to warm to RT and stirred for 2 h. Subsequently, the mixture was quenched with aq. sat. Na2S2O3 and aq. sat. NaHCO3 and was extracted with DCM. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. The residue was dissolved in tert-BuOH (16 mL) and 2-methyl-2-butene (4 mL) and treated at 0° C. dropwise over 30 min with a soln. of NaH2PO4 (2.64 g, 16.9 mmol) and NaClO2 (0.96 g, 8.46 mmol) in H2O (5 mL). The mixture was stirred at RT for 45 min, then, the volatiles were removed in vacuo, the residue was diluted with H2O and extracted with EtOAc. The comb. org. layers were dried over MgSO4 and conc. in vacuo.

Provenance & Evidence