Water → (E)-3-(3-t-Butyl-4-hydroxyphenyl)-2-(4-fluorophenylsulfonyl)acrylonitrile

HRID 1976201

Reaktionsgleichung

Reaktionsgleichung von HRID 1976201
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH2:24][C:25]#[N:26])(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>C(O)C>[C:1]([C:5]1[CH:6]=[C:7](/[CH:8]=[C:24](/[S:21]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)(=[O:23])=[O:22])\[C:25]#[N:26])[CH:10]=[CH:11][C:12]=1[OH:13])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 5657322-(4-Fluorobenzenesulfonyl)acetonitrileHCID 30176183-(tert-Butyl)-4-hydroxybenzaldehyde

Produkt 1

HCID 22000567(E)-3-(3-t-Butyl-4-hydroxyphenyl)-2-(4-fluorophenylsulfonyl)acrylonitrileAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The reaction mixture of 178.0 mg of 3-t-butyl-4-hydroxybenzaldehyde and 219.0 mg of (4-fluorobenzenesulphonyl)acetonitrile in 2.0 mL of ethanol containing 0.01 mL piperidine was refluxed for 4 h and cooled down. To the above reaction mixture was added water and then the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The resulting residue was purified on silica gel column eluting with ethyl acetate-hexane (1:6) to give 295.0 mg of the titled compound.

Aufarbeitung

  1. temperaturewas refluxed for 4 h
  2. temperaturecooled down
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified on silica gel column
  8. washeluting with ethyl acetate-hexane (1:6)

Quellen und Nachweise

ORD-Eintrag
ord-0ff9b479bb8a45d2b56a8c064abba708
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06225346B1

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