Triethylamine → HCID 18353346, Verbindung

HRID 429767

Reaktionsgleichung

Reaktionsgleichung von HRID 429767
[CH3:1][CH:2]([OH:6])[CH2:3][C:4]#[CH:5].BrC1[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1.[CH2:18](N(CC)CC)C>[Cu]I>[OH:6][C:2]([CH3:18])([CH3:1])[C:3]#[C:4][C:5]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 929154-Pentyn-2-olHCID 7363321-(4-Bromophenyl)propan-2-one

Produkt 1

HCID 18353346HCID 18353346, VerbindungAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

0,35 g (0,5 mmol) Pd[TPP]2Cl2 and 0.12 g (=0.6 mmol) of copper(I) iodide and, with stirring in the course of a few minutes, 10.7 g (=0.13 mmol) of 1-methyl-3-butyn-1-ol are added to a solution of 21.3 g (=0.1 mol) of 4-bromophenylacetone in 250 ml of triethylamine. The mixture is warmed to 55° C. and the temperature is allowed slowly to rise to 80° C. during the course of 4 hours. After cooling, the mixture is filtered and the filtrate is concentrated. The oil which remains is chromatographed on silica gel. 17.4 g (90.3% of theory) of 4-(3-hydroxy-3-methyl-1-butynyl)phenylacetone are obtained; m.p. 67-69° C.

Aufarbeitung

  1. customto rise to 80° C. during the course of 4 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. customThe oil which remains is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-001e0c8865ab414f8a62ce2c345515f4
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06319925B1

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