Hydrochloric Acid → 2-(5-Benzyloxypentyl)-2-(3,3,3-trifluoropropyl)malononitrile

HRID 1443595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443595
[F:1][C:2]([F:11])([F:10])[CH2:3][CH2:4][CH:5]([C:8]#[N:9])[C:6]#[N:7].[CH2:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH2:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:5]([CH2:4][CH2:3][C:2]([F:10])([F:11])[F:1])([C:8]#[N:9])[C:6]#[N:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14221121Benzyl 5-Bromoamyl EtherHCID 221857612-(3,3,3-Trifluoropropyl)malononitrile

Produkt 1

HCID 588790442-(5-Benzyloxypentyl)-2-(3,3,3-trifluoropropyl)malononitrileAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

3.5 g of 2-(3,3,3-trifluoropropyl)malononitrile, 5.5 g of 5-bromopentyl benzyl ether and 0.70 g of potassium iodide were dissolved in 20 ml of dimethyl sulfoxide, 3.3 g of potassium carbonate was added, and the mixture was stirred at room temperature for 9 hours. Thereafter, dilute hydrochloric acid was added to the reaction mixture, followed by extraction with methyl tert-butyl ether. The organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 5.9 g of 2-(5-benzyloxypentyl)-2-(3,3,3-trifluoropropyl)malononitrile.

Aufarbeitung

  1. extractionfollowed by extraction with methyl tert-butyl ether
  2. washThe organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-191b6dfc0f254c298d0b3c0ebf7af502
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662402B2

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