4-Hydroxy-3-iodobenzaldehyde → HCID 10615412, Verbindung

HRID 1755948

Reaktionsgleichung

Reaktionsgleichung von HRID 1755948
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]#[CH:15].[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=1I>N1C=CC=CC=1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][C:14]1[O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=2[CH:15]=1

Komponenten

5

Edukt 2

HCID 9688814-Hydroxy-3-iodobenzaldehydeHCID 10535929Oxazole, 5-methyl-2-phenyl-4-(2-propynyl)-

Produkt 1

HCID 10615412HCID 10615412, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 1049PyridineLösungsmittel3×

Versuchsvorschrift

To a slurry of cuprous oxide (12 g, 84 mmol) in pyridine (150 ml) were added a solution of 5-methyl-2-phenyl-4-(2-propynyl) oxazole in pyridine (150 ml) followed by a solution of 4-hydroxy-3-iodobenzaldehyde (35 g, 0.14 mol) in pyridine (100 ml). Bis(triphenyl-phosphine) palladium (II) chloride (0.50 g, 0.7 mmol) was then added as a solid and the mixture was heated to reflux overnight. The mixture was cooled and concentrated. The residue was taken up in ethyl acetate (250 ml+3×50 ml). The ethyl acetate solution was concentrated and the residue was extracted with hot cyclohexane. The hot solution was filtered and cooled and the solid was collected (29 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. concentrationThe ethyl acetate solution was concentrated
  6. extractionthe residue was extracted with hot cyclohexane
  7. filtrationThe hot solution was filtered
  8. temperaturecooled
  9. customthe solid was collected (29 g)

Quellen und Nachweise

ORD-Eintrag
ord-3b4cdf440c4449918f2a399c9d455c8c
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05438074

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