1,4-Dioxane → HCID 58382000, compound

Participants

Reaction Steps

(E)-3-(2-Styryl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)benzoic acid (0.940 g, 1.99 mmol; prepared using D from Preparation #V.1 with (E)-styrylboronic acid), OsO4 (2.5 wt % in t-BuOH, 1.00 mL, 0.080 mmol) and NaIO4 (1.71 g, 7.97 mmol) were added to a stirred mixture of 1,4-dioxane (10 mL) and water (2 mL) at rt. After about 4.5 h the mixture was diluted with water (30 mL) and extracted with EtOAc (40 mL). The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to provide 3-(2-formyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)benzoic acid (0.792 g, 100%): LC/MS (Table 2, Method c) Rt=1.45 min; MS m/z 398 (M+H)+.

Provenance & Evidence