Water → 1-(5-Indanyl)-2-(3-pyridyl)ethanone

HRID 65039

Reaktionsgleichung

Reaktionsgleichung von HRID 65039
C([Li])CCC.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=1.C[O:14][C:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[CH2:22][CH2:21][CH2:20]2)=O.O>O1CCCC1.C(NC(C)C)(C)C>[CH2:22]1[C:23]2[C:19](=[CH:18][C:17]([C:15](=[O:14])[CH2:12][C:8]3[CH:7]=[N:6][CH:11]=[CH:10][CH:9]=3)=[CH:25][CH:24]=2)[CH2:20][CH2:21]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 79703-MethylpyridineHCID 10464836Methyl 2,3-dihydro-1H-indene-5-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 137146531-(5-Indanyl)-2-(3-pyridyl)ethanoneAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7912DiisopropylamineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 80 ml of anhydrous tetrahydrofuran was dissolved 8.86 ml of diisopropylamine. The solution was cooled to -10°, to which was added dropwise 39.5 ml of a hexanoic solution of n-butyl lithium (1.6M). Then, the mixture was stirred for 30 minutes at the same temperature, followed by dropwise addition of 5.34 g of β-picoline. The mixture was stirred for 30 minutes, to which was added dropwise 5 g of 5-methoxycarbonyl indane dissolved in 10 ml of anhydrous tetrohydrofuran. Then, the mixture was stirred for one hour at room temperature, followed by addition of about 25 ml of water. The organic solvent was exaporated off under reduced pressure. The concentrated solution was subjected to extraction with ethylacetate. The extract solution was washed with water, dried on magnesium sulfate and concentrated. The concentrate was crystallized from ethylacetate-isopropylether to give 5.6 g (yield 82%) of 1-(5-indanyl)-2-(3-pyridyl)-ethanone, m.p. 55°-56° C.

Aufarbeitung

  1. temperatureThe solution was cooled to -10°, to which
  2. stirringThe mixture was stirred for 30 minutes, to which
  3. dissolutiondissolved in 10 ml of anhydrous tetrohydrofuran
  4. stirringThen, the mixture was stirred for one hour at room temperature
  5. extractionThe concentrated solution was subjected to extraction with ethylacetate
  6. washThe extract solution was washed with water
  7. customdried on magnesium sulfate
  8. concentrationconcentrated
  9. customThe concentrate was crystallized from ethylacetate-isopropylether

Quellen und Nachweise

ORD-Eintrag
ord-4cc8ef99277c47c68418628848b35db2
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612321

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