4-Pentyn-1-ol → 5-(2,5-Dichlorophenyl)pent-4-yn-1-ol

HRID 395375

Reaktionsgleichung

Reaktionsgleichung von HRID 395375
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1I.[CH2:10]([OH:15])[CH2:11][CH2:12][C:13]#[CH:14]>C(NCC)C.ClCCl.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:14]#[C:13][CH2:12][CH2:11][CH2:10][OH:15]

Komponenten

6

Edukt 2

HCID 793464-Pentyn-1-olHCID 1224521,4-Dichloro-2-iodobenzene

Produkt 1

HCID 223207595-(2,5-Dichlorophenyl)pent-4-yn-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

A solution of 1,4-dichloro-2-iodobenzene (20.0 g, 73.3 mmol), 4-pentyn-1-ol (6.17 g, 73.3 mmol), bistriphenylphosphine(Pd II) chloride (1.03 g, 1.47 mmol), and copper(I) iodide (0.14 g, 0.733 mmol) in 400 ml of diethylamine was stirred under nitrogen for three days. This was diluted with dichloromethane and the oily layer was adsorbed onto silica gel and eluted with hexanes-ethyl acetate (5:1) to give 5-(2,5-dichlorophenyl)pent-4-yn-1-ol, 13.7 g (82%); NMR (CDCl3) δ 1.9 (m, 2H), 2.6 (t, 2H), 3.85 (t, 2H), 7.2 (dd, 1H), 7.28 (m, 1H), 7.4 (d, 2H).

Aufarbeitung

  1. washeluted with hexanes-ethyl acetate (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-929d5a52771a4fb78e7fade0ed26344a
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605628B1

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