Water → HCID 86676920, compound

Participants

Reaction Conditions

Reaction Steps

4-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-6-[(E)-2-ethoxyvinyl]-2-(trifluoromethyl)pyrimidine (2.50 g, 6.68 mmol) was dissolved in 1,4-dioxane (190 mL,) and water (48 mL) and then sodium periodate (4.3 g, 20. mmol, Aldrich) was added, followed by a 4% solution of osmium tetraoxide in water (1.47 mL, 0.232 mmol). The solution began to form a whitish solid after a few minutes. The reaction was stirred at 25° C. for 48 hours until LCMS analysis of the reaction mixture showed no starting material present. The reaction was transferred to a separatory funnel and partitioned between water and EtOAc, the phases were separated, and then the aqueous phase was washed with EtOAc. The combined organic phase was washed with water, then saturated NaCl, dried over MgSO4 and filtered and stripped to dryness to leave the crude product. The crude material was used in the next reaction without purification. 1H NMR (400 MHz, CDCl3) δ: 10.01 (s, 1H), 7.33 (s, 1H), 5.38 (m, 1H), 3.97 (s, 4H), 1.20-2.05 (m, 8H).

Provenance & Evidence