Hexane → HCID 14835954, Verbindung

HRID 1461285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461285
[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 ml) was treated under an atmosphere of nitrogen with 1.5M-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-c4236ae4f3ae4394a84935f10227ef7a
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05075303

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