Triacetoxyperiodinane → HCID 71257714, compound

Participants

Reaction Conditions

Reaction Steps

1-[6-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl]ethanol (0.20 g, 0.57 mmol) was dissolved in methylene chloride (5.00 mL) and cooled to 0° C. To this mixture, Dess-Martin periodinane (0.292 g, 0.689 mmol) was added. The mixture was stirred at 0° C. for 2 hours and then allowed to warm to 25° C. LCMS analysis indicated the reaction was complete. The mixture was extracted with EtOAc and the EtOAc extract was then washed with NaHCO3, sat. NaCl, dried and then the solvent was removed in vacuo to give the product, which was used in the next reaction. MS: 369 (M+Na+). 1H NMR (500 MHz, CDCl3): δ 7.35 (s, 1H); 5.33 (m, 1H, OCH); 3.95 (s, 411, OCH2); 2.63 (s, 3H, CH3); 1.99 (m, 4H); 1.82 (m, 2H); 1.63 (m, 2H). 13C NMR (125 MHz, CDCl3): δ 198 (s, O═C); 171 (s, OC); 161 (s, NC); 157 (q, N2C); 119 (q, CF3); 108 (s, CH and O2C); 74 (s, OCH); 65 (s, OCH2); 32 (s, CH2); 28 (s, CH2); 26 (s, CH3).

Provenance & Evidence