Hydrochloric Acid → (1-methyl-1H-pyrazol-4-yl)(tetrahydro-2H-pyran-4-yl)methanone

HRID 512202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512202
I[C:2]1[CH:3]=[N:4][N:5]([CH3:7])[CH:6]=1.CON(C)[C:11]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12].Cl>C1COCC1>[CH3:7][N:5]1[CH:6]=[C:2]([C:11]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:12])[CH:3]=[N:4]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 27347731-Methyl-4-iodo-1H-pyrazoleHCID 23144693N-methoxy-N-methyloxane-4-carboxamide

Produkt 1

HCID 65195740(1-methyl-1H-pyrazol-4-yl)(tetrahydro-2H-pyran-4-yl)methanoneAusbeute 29,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 4-iodo-1-methyl-1H-pyrazole (0.80 g, 3.9 mmol) in THF (7.04 g, 8.00 ml, 98 mmol) was cooled at 0° C. A solution of isopropylmagnesium chloride lithium chloride complex in THF (5.42 ml, 4.23 mmol, 0.78 molar) was added dropwise and the reaction was stifled for 1½ hour. A solution of N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide (0.733 g, 4.23 mmol) in THF (2 mL) was added dropwise. Cooling was removed after 15 min and reaction was then stirred for 2 hours. To the mixture was added 2 M HCl (20 mL) and it was extracted with AcOEt (3×25 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography to yield (1-methyl-1H-pyrazol-4-yl)(tetrahydro-2H-pyran-4-yl)methanone (220 mg, 1.13 mmol, 29.4% yield).

Aufarbeitung

  1. waitthe reaction was stifled for 1½ hour
  2. temperatureCooling
  3. customwas removed after 15 min
  4. customreaction
  5. extractionwas extracted with AcOEt (3×25 mL)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-94ae3f38bac84226b2226bf13061879a
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102591B2

Notizen zur Reaktion

Wird geladen…