Triacetoxyperiodinane → 6-(Trifluoromethyl)pyridine-3-carboxaldehyde

HRID 1515357Notes

Reaction equation

HRID 1515357 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC.[OH-].[Na+]>[F:12][C:2]([F:1])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[O:10])=[CH:7][N:8]=1

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 36138956-(Trifluoromethyl)pyridine-3-methanol

Product 1

HCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeYield 45%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of [6-(trifluoromethyl)pyridine-3-yl]methanol (0.886 g, 5.0 mmol) in DCM (20 ml) was added to a mixture of Dess-Martin periodinane (2.334 g, 5.5 mmol) in DCM (20 ml) at rt. The reaction was stirred for 1.5 hrs then diluted with Et2O (100 ml) and 4N NaOH (15 ml). The mixture was stirred for 10 mins then separated. The organic layer was washed with 4N NaOH (15 ml) then brine, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (silica, 15% EtOAc/hexanes) to give the aldehyde (0.392 g, 45%). 1HNMR (400 MHz, CDCl3): δ 7.89 (1H, d, J 8.1), 8.37 (1H, d, J 8.1), 9.20 (1H, s), 10.22 (1H, s).

Workup

  1. stirringThe mixture was stirred for 10 mins
  2. customthen separated
  3. washThe organic layer was washed with 4N NaOH (15 ml)
  4. dry with materialbrine, dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (silica, 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-da494e90425c480d91cd315c664dfee9
Source dataset
uspto-grants-2012_07
Patent number
US08222418B2

Reaction notes

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