4-Chlorophenol → Methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate

HRID 1977408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1977408
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9]C(C)([O-])C.[K+].Cl[C:16]1[CH:17]=[N:18][CH:19]=[C:20](Cl)[C:21]=1[CH:22]=O.C[CH:26]([SH:30])[C:27]([O-:29])=[O:28].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:20]2[CH:19]=[N:18][CH:17]=[C:16]3[S:30][C:26]([C:27]([O:29][CH3:9])=[O:28])=[CH:22][C:21]=23)=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 156077362-MercaptopropionateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 10892544Methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 4-chlorophenol (2.63 g, 20.5 mmol) in THF (20 mL) at 0° C. was treated dropwise with a solution of potassium tert-butoxide (1.0 M solution in THF, 20.4 mL, 20.5 mmol), stirred at 25° C. for 1 hour, cooled to 0° C., treated with a solution of Example 17A (3.54 g, 20.23 mmol) in THF (40 mL), warmed at 60° C. for 0.5 hours, cooled to 0° C., treated with methylthioglycolate (1.989 mL, 22.25 mmol) and Cs2CO3 (6.59 g, 20.23 mmol), warmed at 60° C. for 0.25 hours, cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate, washed sequentially with water and brine, dried (MgSO4), filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 4% acetone/hexane provided the title compound.

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. temperaturewarmed at 60° C. for 0.5 hours
  3. temperaturecooled to 0° C.
  4. temperaturewarmed at 60° C. for 0.25 hours
  5. temperaturecooled to room temperature
  6. filtrationfiltered
  7. additionThe filtrate was diluted with ethyl acetate
  8. washwashed sequentially with water and brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification of the residue by flash chromatography on silica gel with 4% acetone/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4aa5b9a27a5f4f1db42c118260a2621f
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06232320B1

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