N,N,N',N'-Tetramethylethylenediamine → HCID 73986572, Verbindung

HRID 840079

Reaktionsgleichung

Reaktionsgleichung von HRID 840079
Br[C:2]1(Br)[CH2:4][C:3]1(Br)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C([Li])CCC.CN(C)CCN(C)C.Br[CH2:26][CH:27]=[CH:28][CH2:29][CH3:30]>O1CCCC1.O>[CH2:26]([C:2]1[CH2:4][C:3]=1[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:27]=[CH:28][CH2:29][CH3:30]

Komponenten

7

Edukt 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 1407151-Bromo-pent-2-eneHCID 14972853HCID 14972853, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 73986572HCID 73986572, VerbindungAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1.00 g (0.00287 mol) of 1,1,2-tribromo-2-pentyl-cyclopropane in 4 ml of tetrahydrofuran was placed under an inert atmosphere of nitrogen via a Firestone valve. To this mixture, cooling in an ice water bath, was added via syringe 3.58 ml (0.00861 mol) of 1.6M n-butyllithium in hexanes. After 30 minutes, 0.432 ml (0.00287 mol) of tetramethylethylene diamine and 0.339 ml (0.00287 mol) of 1-bromo-2-pentene were added by syringe. The reaction stirred for one hour while warming to room temperature, then for three hours at room temperature. To the resulting mixture was added 2 ml of water. This residue was extracted with diethyl ether. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo to yield 0.200 g (39.1% of theory) of 1-pent-2-enyl-2-pentyl-cyclopropene as an oil.

Aufarbeitung

  1. temperatureTo this mixture, cooling in an ice water bath
  2. waitfor three hours at room temperature
  3. extractionThis residue was extracted with diethyl ether
  4. customThe resulting mixture was transferred to a separatory funnel
  5. customthe phases were separated
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e21118d2c93f4115a629f2705b287859
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06365549B2

Verknüpfte Notizen

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