Thionyl Chloride → 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole

HRID 629390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629390
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=2)=[N:3]1.S(Cl)([Cl:17])=O>C1COCC1.O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:17][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)=[CH:8][CH:9]=1

Komponenten

7

Edukt 2

HCID 24386Thionyl ChlorideHCID 24229469[4-(1-methyl-1H-pyrazol-3-yl)phenyl]methanol

Produkt 1

HCID 242294723-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
17 °C

Versuchsvorschrift

To a solution of [4-(1-methyl-1H-pyrazol-3-yl)phenyl]methanol (1.00 g) in THF (15.0 mL) was added dropwise thionyl chloride (0.58 mL) under ice-cooling, and the mixture was stirred at 17° C. for 16 hr. The reaction mixture was diluted with water and ethyl acetate, and saturated aqueous sodium bicarbonate was added thereto. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.65 g).

Aufarbeitung

  1. temperaturecooling
  2. additionwas added
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d1e855cd929b4e5a868c5be7091b62b2
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315458B2

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