1-(2-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde → cyclohexyl[1-(2-methoxyphenyl)-3-methyl-1H-pyrazol-4-yl]methanol

HRID 2090934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090934
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[C:12]([CH:14]=[O:15])[C:11]([CH3:16])=[N:10]1.[CH:17]1([Mg]Br)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>O1CCCC1>[CH:17]1([CH:14]([C:12]2[C:11]([CH3:16])=[N:10][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH:13]=2)[OH:15])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

4

Edukt 2

HCID 630357731-(2-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde2×HCID 178419651HCID 178419651, Verbindung

Produkt 1

HCID 66777925cyclohexyl[1-(2-methoxyphenyl)-3-methyl-1H-pyrazol-4-yl]methanolAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution (15 mL) of 1-(2-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde (1.5 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added dropwise under ice-cooling cyclohexylmagnesium bromide (11.0 mL, 1M tetrahydrofuran solution). After the completion of the dropwise addition, the ice bath was removed, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (1.1 g, 53%) as a pale-yellow oil.

Aufarbeitung

  1. additionwas added dropwise under ice-
  2. additionAfter the completion of the dropwise addition
  3. customthe ice bath was removed
  4. additionTo the reaction mixture was added aqueous ammonium chloride solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

Quellen und Nachweise

ORD-Eintrag
ord-0159c50d04624f50ab8b39f253670291
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436043B2

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