Hexane → 3,4-Dihydro-2-naphthalenylacetonitrile

HRID 330275

Reaktionsgleichung

Reaktionsgleichung von HRID 330275
CCCCCC.[H-].[Na+].[C:9]([CH2:11]P(=O)(OCC)OCC)#[N:10].[CH2:20]1[C:29](=O)[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1>C1COCC1.O>[C:21]1([CH2:11][C:9]#[N:10])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:28][CH2:29][CH:20]=1

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 682662-TetraloneHCID 75676Diethyl (cyanomethyl)phosphonate

Produkt 1

HCID 27778183,4-Dihydro-2-naphthalenylacetonitrileAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mechanically stirred mixture of hexane washed sodium hydride (8.98 g, 0.187 mol, 50%/mineral oil) in THF (400 mL) was added diethyl cyanomethylphosphonate (33.13 g, 0.187 mol) dropwise. The reaction was stirred at room temperature for 1/2 hour. β-Tetralone (24.8 g, 0.170 mol) in THF (100 mL) was added dropwise at 0° C., and the reaction was stirred at room temperature for 1 hour. The reaction was diluted with water (600 mL) and extracted with ether (3×400 mL). The organic phase was washed with brine, dried (MgSO4), and concentrated under reduced pressure to give an orange oil. Distillation from bulb to bulb under high vacuum yielded 22.65 g (79%) of product as a pale yellow oil.

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature for 1 hour
  2. extractionextracted with ether (3×400 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give an orange oil
  7. distillationDistillation from bulb to bulb under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5d5b182bb2b5485f9bd2ebb037d9f587
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04895860

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