Triacetoxyperiodinane → HCID 24800521, compound

HRID 386467Notes

Reaction equation

HRID 386467 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[O:13][C:12]([CH:14]([OH:31])[CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:19][CH:18]=3)=[N:11][CH:10]=2)[N:4]=1)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[O:13][C:12]([C:14](=[O:31])[CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][O:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:19][CH:18]=3)=[N:11][CH:10]=2)[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 24800520HCID 24800520, compound

Product 1

HCID 24800521HCID 24800521, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Cyano-6-(2-(1-hydroxy-3-(4-(phenoxymethyl)phenyl)propyl)oxazol-5-yl)pyridine (133 mg, 0.323 mmol) was dissolved in anhydrous CH2Cl2 (4 mL) and Dess-Martin periodinane (205 mg, 0.485 mmol) was added. The reaction solution was stirred at room temperature under an atmosphere of Ar for 2.5 h. The addition of saturated aqueous NaHCO3 quenched the reaction and the organic layer was washed with saturated aqueous Na2S2O3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4 and the solvent was removed in vacuo. The crude product was purified by flash chromatography (SiO2, 0-1% MeOH/CH2Cl2) to provide 2-cyano-6-(2-(3-(4-(phenoxymethyl)phenyl)propanoyl)oxazol-5-yl)pyridine as a yellow solid (98 mg, 74%): 1H NMR (CDCl3, 500 MHz) δ 8.04 (dd, 1H, J=8.1, 0.9 Hz), 7.98-7.95 (m, 2H), 7.68 (dd, 1H, J=7.7, 0.9 Hz), 7.37 (d, 2H, J=8.0 Hz), 7.30-7.26 (m, 4H), 6.97-6.94 (m, 3H), 5.03 (s, 2H), 3.74 (t, 2H, J=7.5 Hz), 3.12 (t, 2H, J=7.5 Hz); 13C NMR (CDCl3, 150 MHz) δ 187.3, 158.7, 157.5, 151.4, 147.8, 140.0, 138.4, 135.1, 134.3, 129.4, 128.5, 128.7, 128.1, 127.8, 123.0, 120.9, 116.5, 114.8, 69.7, 40.7, 29.3; HR ESI-TOF m/z 410.1501 (M+H+, C25H19N3O3, requires 410.1499).

Workup

  1. customquenched
  2. customthe reaction
  3. washthe organic layer was washed with saturated aqueous Na2S2O3 and saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography (SiO2, 0-1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-dd4eb02280284f809ece3216fd6e683b
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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