Hexane → HCID 14835954, Verbindung

HRID 1613585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613585
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.C([Li])CCC.CCCCCC.[C:23]1([Se:29]Cl)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1.O>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([Se:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 21928ChloroselenobenzeneHCID 1200283-Methyl-5,6,7,8-tetrahydroquinolineHCID 178418339Butyllithium

Produkt 1

HCID 14835954HCID 14835954, VerbindungAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 5,6,7,8-tetrahydro-3-methylquinoline (7.5 g, 51 mmol) in tetrahydrofuran (100 mI) was treated under an atmosphere of nitrogen with 1.5%-butyllithium in hexane (35 ml, 52 mmol) at 0°. The resulting red solution was added to a solution of phenylselenyl chloride (10 g, 52 mmol) in tetrahydrofuran (50 ml) at 0°. After 30 min, water (100 ml) was added and the mixture concentrated in vacuo. The aqueous residue was partitioned between saturated aqueous sodium chloride (100 ml) and ether (100 ml). The organic phase was dried (Na2SO4) and evaporated in vacuo to give the crude product (15.2 g) as an oil.

Aufarbeitung

  1. concentrationthe mixture concentrated in vacuo
  2. customThe aqueous residue was partitioned between saturated aqueous sodium chloride (100 ml) and ether (100 ml)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-60daca0822bd4eda926d6cbaee4fe25c
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194439

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