Propargyl alcohol → 3-Hydroxy-1-[4-chloro-2-benzoylphenyl]propyne

HRID 2166662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2166662
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24](I)=[C:25]([CH:34]=1)[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27].[CH2:36]([OH:39])[C:37]#[CH:38]>[Pd](Cl)Cl.C(NCC)C>[OH:39][CH2:36][C:37]#[C:38][C:24]1[CH:23]=[CH:22][C:21]([Cl:20])=[CH:34][C:25]=1[C:26](=[O:27])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 3

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 129482625-Chloro-2-iodobenzophenone

Produkt 1

HCID 128416443-Hydroxy-1-[4-chloro-2-benzoylphenyl]propyne

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

A mixture of 0.17 g (1.0 mmole) of palladium chloride, 0.5 g (2.0 mmole) of triphenylphosphine, 0.1 g (0.5 mmole) of cuprous iodide, 15 g (43 mmole) of 5-chloro-2-iodobenzophenone and 60 ml of diethylamine was stirred at room temperature for 20 min. In one portion 6.0 g (107 mmole) of propargyl alcohol was added, and the resulting mixture was stirred for 24 hr. The solvent was removed at reduced pressure and the residue was dissolved in ether. The ether solution was washed with water, dried with anhydrous sodium sulfate, and concentrated at reduced pressure to give the product as a red oil.

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 24 hr
  2. customThe solvent was removed at reduced pressure
  3. dissolutionthe residue was dissolved in ether
  4. washThe ether solution was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2218bc03aee44663897cef1ab09b7063
Quelldatensatz
uspto-grants-1983_06
Patentnummer
US04388239

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