2-Ethylbutyraldehyde → 2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butan-1-ol

HRID 748036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748036
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1.[Li]CCCC.[CH2:20]([CH:22]([CH2:25][CH3:26])[CH:23]=[O:24])[CH3:21]>C1COCC1>[CH2:20]([CH:22]([CH2:25][CH3:26])[CH:23]([C:12]1[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][CH:13]=2)[N:9]=[CH:10][CH:11]=1)[OH:24])[CH3:21]

Komponenten

5

Edukt 3

HCID 73592-EthylbutyraldehydeHCID 102417081-(4-Methoxybenzyl)-1H-pyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 685942442-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butan-1-olAusbeute 44,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 1-(4-methoxybenzyl)-1H-pyrazole (Synthetic Comm. 25(5), 761-774 (1995)) (2.43 g, 12.9 mmol) in THF (100 mL) at −78° C. was added a solution of n-BuLi (2 M in cyclohexane, 7.1 mL, 14.2 mmol) dropwise. After 75 min, 2-ethylbutyraldehyde (1.3 mL, 10.6 mmol) was added. After 45 min the reaction mixture was quenched with saturated aqueous ammonium chloride (50 mL), extracted with EtOAc (3×100 mL), dried (Na2SO4) and concentrated. Column chromatography (EtOAc/hexanes, 1:4) provided 1.37 g (37%) of 2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butan-1-ol as an oil.

Aufarbeitung

  1. customAfter 45 min the reaction mixture was quenched with saturated aqueous ammonium chloride (50 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e6366a35082b4238a85a29cf6b5dc0f6
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399778B2

Notizen zur Reaktion

Wird geladen…