Triacetoxyperiodinane → 5-(Trifluoromethyl)pyridine-2-carbaldehyde

A solution of Example 34B (3.89 g, 22.0 mmol) in CH2Cl2 (10 mL) was added to a deoxygenated solution of Dess-Martin periodinane (1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one, 10.3 g, 24.2 mmol) in CH2Cl2 (73 mL) in one portion. The reaction was stirred under nitrogen at ambient temperature for about 20 minutes after which a solid formed. The reaction was diluted with 50 mL CH2Cl2 and carefully quenched with approximately 30 mL of saturated NaHCO3 solution. The undissolved solid was filtered, and the filtrate was transferred to a separatory funnel. The aqueous phase was extracted with CH2Cl2, and the combined organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated at reduced pressure to 50 mL. This solution was then loaded on silica gel (Analogix® 40×150 column) and eluted with 25% to 50% EtOAc/hexanes. The result was 2.86 g (74%) of the title compound as a clear oil, which solidified on standing. 1H NMR (300 MHz, CDCl3) δ 10.15 (s, 1H), 9.06 (m, 1H), 8.15 (m, 1H), 8.09 (d, J=8.1, 1H).

1. customformed
2. customcarefully quenched with approximately 30 mL of saturated NaHCO3 solution
3. filtrationThe undissolved solid was filtered
4. customthe filtrate was transferred to a separatory funnel
5. extractionThe aqueous phase was extracted with CH2Cl2
6. washthe combined organic layer was washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customevaporated at reduced pressure to 50 mL
10. washeluted with 25% to 50% EtOAc/hexanes

ORD record

ord-f016bc5877104bd884e9d55525a36c73

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998993B2