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

HRID 1166093Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

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)+.

Workup

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)

Sources & evidence

ORD record: ord-7c861f51a31c4e799360860a92b4a99d
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613747B2

Reaction notes

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