Triacetoxyperiodinane → Methyl 6-formylpyridine-3-carboxylate

HRID 341519

Reaktionsgleichung

Reaktionsgleichung von HRID 341519
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][C:25]1[N:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[CH:24]([C:25]1[N:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1)=[O:23]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 7894146-Hydroxymethyl-nicotinic acid methyl ester2×

Produkt 1

HCID 586269Methyl 6-formylpyridine-3-carboxylateAusbeute 105 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Dess-Martin periodinane (2.54 g, 5.98 mmol) was added to a solution of methyl 6-(hydroxymethyl)pyridine-3-carboxylate (Intermediate 190, 1.00 g, 5.98 mmol) in DCM (75 mL) at room temperature. The reaction mixture was stirred at room temperature for 24 hrs before being diluted with DCM (50 mL), washed with a 1:1 mixture of saturated aqueous solution of sodium bicarbonate and sodium thiosulfate (3×75 mL). The organic phase was dried over sodium sulfate, filtered and evaporated under vacuum to provide the title compound (1.02 g, 105%). Method B HPLC-MS: MH+ requires m/z=166 Found: m/z=166, Rt=1.44 min (62%).

Aufarbeitung

  1. washwashed with a 1:1 mixture of saturated aqueous solution of sodium bicarbonate and sodium thiosulfate (3×75 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b231342f377b4faeb25c62d2e8ca62f1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895733B2

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