Triacetoxyperiodinane → HCID 76694887, compound

Participants

Reaction Steps

1-[8-Chloro-3-(3-hydroxypropyl)-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-2-yl]ethanone (4-4; a racemic mixture, 15 mg, 39 μmol) was dissolved in anhydrous CH2Cl2 (2 mL) and was treated with Dess-Martin periodinane (25 mg, 58 μmol) and the resulting cloudy yellow solution was stirred 1.5 h. Upon completion, the cloudy solution was treated with 1 mL sat. sodium thiosulfate/NaHCO3 solution (1:1) and stirred 30 min. The mixture was extracted with EtOAc (3×5 mL), and the combined organics were dried (MgSO4), filtered and concentrated. The crude residue 3-(2-acetyl-8-chloro-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-3-yl)propanal (4-5; a racemic mixture) was carried directly into the next transformation.

Provenance & Evidence