Sodium Hydroxide → HCID 22047127, Verbindung

HRID 1830535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1830535
[Cl:1][C:2]1[N:3]=[C:4]([CH:11]=[O:12])[CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12.[OH:13]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+].[OH-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[N:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 516951Monobasic potassium phosphateHCID 10535409HCID 10535409, VerbindungHCID 23668197Sodium Chlorite

Produkt 1

HCID 22047127HCID 22047127, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

C6 (3.0 g, 16.5 mmol) is dissolved in 40 mL DMSO. KH2PO4 (561 mg, 4.1 mmol) in 6.5 mL water is added and then NaClO2 (2.6 g, 23.1 mmol) in 24 mL water is added, and the reaction is stirred overnight at rt. The reaction is diluted with 200 mL water, the pH is adjusted to 9 with 2N NaOH, and any remaining aldehyde is extracted into 3×50 mL ether. The pH of the aqueous layer is adjusted to 3 with 10% aqueous HCl and is extracted with 4×50 mL EtOAc. The combined organic layer is dried over anhydrous MgSO4, filtered, and then concentrated in vacuo to a white solid. The solid is washed with ether and is dried to afford 7-chlorofuro[2,3-c]pyridine-5-carboxylic acid (C7) (55% yield). MS (CI) for C8H4ClNO3, m/z: 198 (M+H)+.

Aufarbeitung

  1. extractionany remaining aldehyde is extracted into 3×50 mL ether
  2. extractionis extracted with 4×50 mL EtOAc
  3. dry with materialThe combined organic layer is dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a white solid
  6. washThe solid is washed with ether
  7. customis dried

Quellen und Nachweise

ORD-Eintrag
ord-3488b172d2df434c9cf8704b223bffc2
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067515B2

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