3-(Methylthio)picolinaldehyde → 3-Methanesulfinyl-pyridine-2-carbaldehyde

HRID 7177

Reaktionsgleichung

Reaktionsgleichung von HRID 7177
[CH3:1][S:2][C:3]1[C:4]([CH:9]=[O:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[OH:11]OS([O-])=O.[K+]>CO.O.C(Cl)Cl>[CH3:1][S:2]([C:3]1[C:4]([CH:9]=[O:10])=[N:5][CH:6]=[CH:7][CH:8]=1)=[O:11]

Komponenten

6

Edukt 2

HCID 139052313-(Methylthio)picolinaldehydeHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 220188063-Methanesulfinyl-pyridine-2-carbaldehydeAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cold (0° C.), stirred solution of 3-methylsulfanyl-pyridine-2-carbaldehyde (prepared as described for AMD9574) (280 mg, 1.83 mmol) in a mixture of MeOH (20 mL) and water (2 mL) was added solid oxone (2.25 g, 3.66 mmol) and the resulting heterogeneous mixture was stirred for 5 h. At this point, the reaction mixture was diluted with CH2Cl2 (50 mL), and then filtered through celite, washed with CH2Cl2 (3×20 mL) and concentrated and dried in vacuo. Flash chromatography (silica gel, 4:1 hexanes-EtOAc) of the residue thus obtained afforded 70 mg (23%) of 3-methanesulfinyl-pyridine-2-carbaldehyde. 1H NMR (CDCl3) □ 2.86 (s, 3H), 7.81 (dd, 1H, J=8, 5 Hz), 8.66–8.69 (m, 1H), 8.90 (d, 1H, J=3 Hz), 10.12 (s, 1H).

Aufarbeitung

  1. filtrationfiltered through celite
  2. washwashed with CH2Cl2 (3×20 mL)
  3. concentrationconcentrated
  4. customdried in vacuo
  5. customFlash chromatography (silica gel, 4:1 hexanes-EtOAc) of the residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-f57dfddb92f34d988cc9313ce5f4d5bb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084155B2

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