Dichloromethane → 1-Ethoxy-2-cyano-5-(naphth-1-yl)-1-pentene

HRID 1081619

Reaktionsgleichung

Reaktionsgleichung von HRID 1081619
[CH2:1]([O:3][CH:4]=[CH:5][C:6]#[N:7])[CH3:2].C([Li])CCC.[C:13]1([CH2:23][CH2:24][CH2:25]I)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(Cl)Cl>O1CCCC1>[CH2:1]([O:3][CH:4]=[C:5]([C:6]#[N:7])[CH2:25][CH2:24][CH2:23][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 436013-Ethoxy-2-propenenitrileHCID 199555551-(3-Iodopropyl)naphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 538620191-Ethoxy-2-cyano-5-(naphth-1-yl)-1-penteneAusbeute 26,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under a nitrogen atmosphere a stirred solution of 1.5 mL (0.014 mole) of 3-ethoxyacrylonitrile in 45 mL of tetrahydrofuran was cooled to about -110° C., and 6.2 mL (0.015 mole) of 2.5M n-butyllithium in hexanes was added dropwise at a rate to keep the reaction mixture temperature below -65° C. Upon completion of addition, the reaction mixture was stirred for about ten minutes, and then a solution of 4.0 grams (0.014 mole) of 3-(naphth-1-yl)propyl iodide in 15 mL of tetrahydrofuran was added dropwise. Upon completion of addition, the reaction mixture was stirred at about -78° C. for two hours. After this time the reaction mixture was allowed to warm to ambient temperature as it stirred for about 16 hours. The reaction mixture was concentrated under reduced pressure, yielding a dark residual oil. The oil was passed through a short column of silica gel using methylene chloride as the eluant. The eluate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished using 2:1 methylene chloride and petroleum ether. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.0 gram of 1-ethoxy-2-cyano-5-(naphth-1-yl)-1-pentene. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. customthe reaction mixture temperature below -65° C
  2. additionUpon completion of addition
  3. additionUpon completion of addition
  4. stirringthe reaction mixture was stirred at about -78° C. for two hours
  5. stirringstirred for about 16 hours
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customyielding a dark residual oil
  8. concentrationThe eluate was concentrated under reduced pressure to a residual oil
  9. washElution
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a47cd9998bdc4490b8aaf3ad71f2fbc1
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587379

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