2-Chloro-1,1-dimethoxyethane → 1-(3,3-dimethoxy-1-phenylpropyl)-1H-pyrazole

HRID 1778842

Reaktionsgleichung

Reaktionsgleichung von HRID 1778842
[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.Cl[CH2:19][CH:20]([O:23][CH3:24])[O:21][CH3:22]>O1CCCC1>[CH3:22][O:21][CH:20]([O:23][CH3:24])[CH2:19][CH:1]([N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 609862-Chloro-1,1-dimethoxyethaneHCID 35464411-Benzyl-1H-pyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 866812991-(3,3-dimethoxy-1-phenylpropyl)-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyl-1H-pyrazole (0.653 g) in tetrahydrofuran (5 mL) cooled to −78° C. was dropwise added 1.6M n-butyllithium (2.84 mL). The reaction mixture was stirred for 60 minutes, and 2-chloro-1,1-dimethoxyethane (0.517 mL) was added, and stirring continued for 3 hours. The reaction mixture was allowed to slowly warm up to room temperature, and was quenched with water, extracted with ether, dried over Na2SO4, filtered, and concentrated. The product was purified by chromatography on silica gel using 0-20% ethyl acetate/hexanes as the eluent to provide the title compound.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 3 hours
  3. customwas quenched with water
  4. extractionextracted with ether
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by chromatography on silica gel using 0-20% ethyl acetate/hexanes as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-6057d7d755654d4cb8bf6e3e3d06020e
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266877B2

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