4-Methyloxybenzyl chloride → 1-(4-Methoxy-benzyl)-cyclopropanecarbonitrile

HRID 408506

Reaktionsgleichung

Reaktionsgleichung von HRID 408506
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH:11]1([C:14]#[N:15])[CH2:13][CH2:12]1.Cl[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1>O1CCCC1>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C:11]2([C:14]#[N:15])[CH2:13][CH2:12]2)=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 699934-Methyloxybenzyl chlorideHCID 79637CyclopropanecarbonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Produkt 1

HCID 574569501-(4-Methoxy-benzyl)-cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Sodium bis(trimethylsilyl)amide (2 M in tetrahydrofuran (THF), 37.5 mL, 75.0 mmol) was slowly added to a solution of cyclopropanecarbonitrile (3.35 g, 49.9 mmol) in THF (30 mL) at room temperature. The reaction mixture was stirred for 20 minutes and then a solution 1-chloromethyl-4-methoxy-benzene (7.83 g, 50.0 mmol) in THF was added. The mixture was heated to reflux for 3 hours and then quenched with a saturated aqueous solution of ammonium chloride (50 mL). The separated aqueous layer was extracted three times with ethyl acetate (50 mL). The combined organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give crude 1-(4-methoxy-benzyl)-cyclopropanecarbonitrile, which was used directly in the next step.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customquenched with a saturated aqueous solution of ammonium chloride (50 mL)
  4. extractionThe separated aqueous layer was extracted three times with ethyl acetate (50 mL)
  5. washThe combined organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  6. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9b5c119074c64264ada051e42bd3a2b9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759335B2

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