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

HRID 227238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227238
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7426a613c0704460af664f96b279241b
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560462B2

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