Hexane → 2-Dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthalene

HRID 233947

Reaktionsgleichung

Reaktionsgleichung von HRID 233947
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2.C([Li])CCC.CCCCCC.[CH3:30][S:31]SC>O1CCCC1.O>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([S:31][CH3:30])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH3:15]

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 12232Dimethyl DisulfideHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 99037352-Dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthaleneAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene (600 mg, 1.93 mMol) in tetrahydrofuran (20 mL) at -78° C. was added a solution of n-butyllithium in hexane (1.6M, 1.9 mL, 3.04 mMol). The solution was stirred at -78° C. for one hour, forming a light orange solution. Dimethyl disulfide (0.24 mL, 3.00 mMol) was added, and the reaction mixture was allowed to warm gradually to room temperature. The colorless solution was diluted with water and extracted with dichloromethane. The dichloromethane extracts were combined, dried (Na2SO4), and concentrated in vacuo to give the crude product as a light yellow oil. Purification by flash chromatography (3% methanol in dichloromethane + tr. NH4OH) gave the product as a colorless, viscous oil (430 mg, 80%). The hydrochloride salt was formed. Recrystallization (ethanol/diethyl ether) gave a colorless, crystalline solid (m.p.=185° C.).

Aufarbeitung

  1. customforming a light orange solution
  2. temperatureto warm gradually to room temperature
  3. extractionextracted with dichloromethane
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product as a light yellow oil
  7. customPurification by flash chromatography (3% methanol in dichloromethane + tr. NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-4a7843a32e0d41108f74b3d1a6a3928b
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594034

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