Propargyl alcohol → 3-(4-Chloro-3-methylphenyl)-2-propyne-1-ol

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Propargyl alcohol	HCID 7859	—
Edukt	Triphenylphosphine	HCID 11776	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	2-Chloro-5-iodotoluene	HCID 4200996	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Katalysator	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Lösungsmittel	Tetrahydrofuran	HCID 8028	—
Lösungsmittel	Sodium chloride; water	HCID 57417360	—
Produkt	3-(4-Chloro-3-methylphenyl)-2-propyne-1-ol	HCID 59407828	—

Reaktionsschritte

A mixture of 2-chloro-5-iodotoluene (5.00 g), copper(I) iodide (75.4 mg), triphenylphosphine (260 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (410 mg), propargyl alcohol (1.29 ml), diisopropylethylamine (13.8 ml) and tetrahydrofuran (80 ml) was stirred at room temperature for 8 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20) to give the object product (3.08 g) as a brown solid.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08129361B2
Quelldatensatz	uspto-grants-2012_03
ORD ID	ord-46b3be13b86d481f820ea1d152976c02
Quellennotiz	uspto-grants-2012_03