p-Toluenesulfonic acid → Pirandamine

HRID 1731144

Reaktionsgleichung

Reaktionsgleichung von HRID 1731144
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][C:5](=O)[CH3:6].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][CH2:30][OH:31])=[CH:21]1.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1.O>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][C:5]1([CH3:6])[C:21]2[CH2:20][C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]=2[CH2:29][CH2:30][O:31]1

Komponenten

7

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 8000Boron trifluoride etherateHCID 5469134-(Dimethylamino)butan-2-oneHCID 113556481H-Indene-3-ethanol

Produkt 1

HCID 431429Pirandamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-dimethylamino-3-butanone (1.0 g) dissolved in toluene (10 ml), p-toluenesulfonic acid (1.3 g) is added. The suspension is stirred for 10 min. Indene-3-ethanol (1.0 g) in toluene (5 ml) is added to the suspension and the resulting solution stirred for 2 hr. Boron trifluoride etherate (0.25 ml) is added together with ca. 0.5 g of hydrated alkali-aluminum silicate. The mixture is heated at 80° C for 30 min. The mixture is cooled and diluted with water. The organic layer is separated and the aqueous layer extracted with toluene. The organic layers are washed with water. The combined aqueous phase is rendered alkaline with conc.NH4OH and extracted with toluene. The latter extract is treated with charcoal and then concentrated to afford the title compound, identical to the compound of the same name described in Example 284.

Aufarbeitung

  1. stirringthe resulting solution stirred for 2 hr
  2. temperatureThe mixture is cooled
  3. customThe organic layer is separated
  4. extractionthe aqueous layer extracted with toluene
  5. washThe organic layers are washed with water
  6. extractionNH4OH and extracted with toluene
  7. extractionThe latter extract
  8. additionis treated with charcoal
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0aee8ca12c14417f8d9857acf2f2de25
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03995052

Verknüpfte Notizen

Wird geladen…