Ammonium Chloride → alpha-(1-Ethoxymethyl-5-pyrazolyl)-2,3-dichloro-4-methoxy-benzylalcohol

HRID 1721935

Reaktionsgleichung

Reaktionsgleichung von HRID 1721935
C([Li])CCC.[CH2:6]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)[CH3:7].[Cl:15][C:16]1[C:23]([Cl:24])=[C:22]([O:25][CH3:26])[CH:21]=[CH:20][C:17]=1[CH:18]=[O:19].[Cl-].[NH4+]>CCCCCC.O1CCCC1.O>[CH2:6]([O:8][CH2:9][N:10]1[C:14]([CH:18]([OH:19])[C:17]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[C:23]([Cl:24])[C:16]=2[Cl:15])=[CH:13][CH:12]=[N:11]1)[CH3:7]

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 130156892,3-Dichloro-4-methoxybenzaldehydeHCID 157143991-(ethoxymethyl)-1H-pyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 14622784alpha-(1-Ethoxymethyl-5-pyrazolyl)-2,3-dichloro-4-methoxy-benzylalcoholAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

4.13 ml of 1.6M n-butyl lithium in hexane are added dropwise to a tetrahydrfuran solution of 0.76 g of 1-ethoxymethylpyrazole at -60° C. under argon gas atmosphere. the mixture is stirred at -63° to -50° C. for 1 hour. A solution of 1.23 g of 2,3-dichloro-4-methoxybenzaldehyde in tetrahydrofuran is added to the mixture, and the mixture is stirred at -50° C. to room temperature for 1 hour. An aqueous saturated ammonium chloride solution and water are added to the mixture under ice-cooling and the mixture is concentrated to remove tetrahydrofuran. The residual aqueous layer is extracted with ethyl acetate and the extract is washed with water, dried and evaporated to give colorless crystals, which are then washed with isopropyl ether and dried to give 1.62 g of α-(1-ethoxymethyl-5-pyrazolyl)-2,3-dichloro-4-methoxy-benzylalcohol.

Aufarbeitung

  1. stirringthe mixture is stirred at -50° C. to room temperature for 1 hour
  2. temperaturecooling
  3. concentrationthe mixture is concentrated
  4. customto remove tetrahydrofuran
  5. extractionThe residual aqueous layer is extracted with ethyl acetate
  6. washthe extract is washed with water
  7. customdried
  8. customevaporated
  9. customto give colorless crystals, which
  10. washare then washed with isopropyl ether
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-80735a99aa4444a89e563646f5f0c8f6
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04853404

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