Propargyl alcohol → 3-[4-(1h-Pyrazol-1-yl)phenyl]-2-propyn-1-ol

HRID 2416450

Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:13]([OH:16])[C:14]#[CH:15]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([C:15]#[C:14][CH2:13][OH:16])=[CH:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=[N:9]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 1-(4-bromophenyl)-1H-pyrazole (prepared as described in Bull. Soc. Chim. Fr. 1966, 2832) (2.24 g, 10.04 mmol), Pd(Ph3P)2Cl2 (180 mg, 0.26 mmol), and copper(I) iodide (95 mg, 0.50 mmol) in TEA (20 mL) was stirred for 5 min, propargyl alcohol (0.70 mL, 12.02 mmol) was added, and the mixture was heated to 80° C. for 48 h. The volatiles were evaporated, ethyl acetate (50 mL) and water (50 mL) were added to the residue, and the mixture was filtered through a pad of Celite. The organic layer from the filtrate was washed with brine (50 mL), dried (Na2SO4), and concentrated. Purification by chromatography (SiO2, 3:2 hexane/ethyl acetate) yielded 0.73 g (37%) of the title compound as a brown solid. MS 199 (M+H)+.

Aufarbeitung

customThe volatiles were evaporated
additionethyl acetate (50 mL) and water (50 mL) were added to the residue
filtrationthe mixture was filtered through a pad of Celite
washThe organic layer from the filtrate was washed with brine (50 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated
customPurification by chromatography (SiO2, 3:2 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-d77c26b8cbdc4eb9b29513f38040abb4
Quelldatensatz: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06825170B2

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