Triacetoxyperiodinane → HCID 86674537, compound

HRID 1888330Notes

Reaction equation

HRID 1888330 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][CH2:25][CH2:26][N:27]1[C:31]([CH2:32][OH:33])=[N:30][C:29]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:28]1>C(Cl)Cl>[CH3:23][O:24][CH2:25][CH2:26][N:27]1[C:31]([CH:32]=[O:33])=[N:30][C:29]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:28]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67257528HCID 67257528, compound

Product 1

HCID 86674537HCID 86674537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (1530 mg, 3.60 mmol) was added to a stirred suspension of [2-(2-Methoxy-ethyl)-5-phenyl-2H-1,2,4-triazol-3-yl]-methanol (840 mg, 3.6 mmol) dissolved in Methylene chloride (36.0 mL) at rt under Ar. The solution was stirred ON. Some solid was filtered off and discarded. Sat NaHCO3 (35 ml) and more DCM (35 ml) were added to the DCM solution. The solvent was evaporated off and the crude product was purified by silica gel chromatography (Eluent: 50% EtOAc in heptane). Yield: 0.76 g of the title compound as an oil. H-NMR: (CDCl3) δ10.04 (s, 1H), 8.13 (m, 2H), 7.45 (m, 3H), 4.82 (t, 2H), 3.83 (t, 2H), 3.32 (s, 3H).

Workup

  1. filtrationSome solid was filtered off
  2. additionSat NaHCO3 (35 ml) and more DCM (35 ml) were added to the DCM solution
  3. customThe solvent was evaporated off
  4. customthe crude product was purified by silica gel chromatography (Eluent: 50% EtOAc in heptane)

Sources & evidence

ORD record
ord-a07a8f314bde48988295c20bf00e8c35
Source dataset
uspto-grants-2013_08
Patent number
US08501795B2

Reaction notes

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