Triacetoxyperiodinane → 2-(4-Methyl-2-nitro-phenyl)thiazole-4-carbaldehyde

HRID 227238Notes

Reaction equation

HRID 227238 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][OH:14])[N:12]=2)=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH:13]=[O:14])[N:12]=2)=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 690554642-(4-Methyl-2-nitro phenyl)thiazol-4-yl methanol

Product 1

HCID 866229132-(4-Methyl-2-nitro-phenyl)thiazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(4-Methyl-2-nitro phenyl)thiazol-4-yl methanol (297 mg, 1.18 mmol) was stirred in 5 mL of CH2Cl2 at room temperature under N2. The Dess-Martin reagent (500 mg, 1.18 mmol) was added as a solid. After 30 minutes, the reaction was complete. The reaction was diluted to 60 mL of CH2Cl2 and washed with 60 mL of 1N NaOH. The organics were dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified on a biotage column 12M eluted with EtOAc/hexanes 1:4 to give the desired material.

Workup

  1. washwashed with 60 mL of 1N NaOH
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified on a biotage column 12M
  6. washeluted with EtOAc/hexanes 1:4

Sources & evidence

ORD record
ord-7426a613c0704460af664f96b279241b
Source dataset
uspto-grants-2009_07
Patent number
US07560462B2

Reaction notes

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