Triacetoxyperiodinane → HCID 24800000, compound

HRID 386447Notes

Reaction equation

HRID 386447 reaction equation
[OH:1][CH:2]([C:18]1[O:19][C:20]([C:23]2[N:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=2)=[CH:21][N:22]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][C:2]([C:18]2[O:19][C:20]([C:23]3[N:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=3)=[CH:21][N:22]=2)=[O:1])=[CH:10][CH:9]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 24799989HCID 24799989, compound

Product 1

HCID 24800000HCID 24800000, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 6-(2-(1-Hydroxy-3-(4-phenoxyphenyl)propyl)oxazol-5-yl)pyridine-3-carboxylate (77 mg, 0.18 mmol) was dissolved in anhydrous CH2Cl2 (2.5 mL) and Dess-Martin periodinane (113 mg, 0.268 mmol) was added. The reaction solution was stirred at room temperature under an atmosphere of Ar for 90 min. The addition of saturated aqueous NaHCO3 quenched the reaction and the organic layer was washed with saturated aqueous Na2S2O3 then 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, 0-50% EtOAc/hexanes) to provide methyl 6-(2-(3-(4-phenoxyphenyl)propanoyl)oxazol-5-yl)pyridine-3-carboxylate as a white solid (63 mg, 82%): 1H NMR (CDCl3, 500 MHz) δ 9.22 (d, 1H, J=1.0 Hz), 8.39 (dd, 1H, J=8.0, 2.0 Hz), 7.97 (s, 1H), 7.91 (d, 1H, J=8.0 Hz), 7.30 (t, 2H, J=7.5 Hz), 7.22 (d, 2H, J=8.5 Hz), 6.93 (d, 2H, J=8.5 Hz), 3.97 (s, 3H), 3.46 (t, 2H, J=7.0 Hz), 3.09 (t, 2H, J=7.0 Hz); 13C NMR (CDCl3, 125 MHz) δ 187.2, 165.0, 157.6, 157.4, 155.5, 152.5, 151.2, 149.2, 138.2, 135.1, 129.7, 129.6, 128.7, 125.8, 123.0, 119.6, 119.1, 118.6, 52.6, 40.8, 28.9; HR ESI-TOF m/z 429.1440 (M+H+, C25H20N2O5, requires 429.1445).

Workup

  1. customquenched
  2. customthe reaction
  3. washthe organic layer was washed with saturated aqueous Na2S2O3
  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, 0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-013ea8b0350440e2a36d1615c26a15d0
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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