Hydrochloric Acid → (4-(Trifluoromethoxy)benzyl)malononitrile

HRID 749601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749601
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:6][CH:5]=1.[BH4-].[Na+].Cl>O1CCCC1.C(O)C>[F:1][C:2]([F:16])([F:17])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 8456624-(Trifluoromethoxy)benzalmalononitrileHCID 4311764Sodium borohydride

Produkt 1

HCID 22235052(4-(Trifluoromethoxy)benzyl)malononitrileAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Then, 2.61 g of (4-(trifluoromethoxy)benzylidene)malononitrile was dissolved in 20 ml of tetrahydrofuran, and while stirring at room temperature, a suspension of 0.11 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloric acid was added, and the mixture was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.20 g of (4-(trifluoromethoxy)benzyl)malononitrile (the intermediate (7)).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringby stirring at room temperature for 30 minutes
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe organic layer was successively washed with 10% hydrochloric acid
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-74ddbc1f80bb47f09eac7b2d43ac95e3
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402691B2

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