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Water → 4-(3,6-dihydro-2H-pyran-4-yl)benzonitrile

HRID 1626746
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1626746
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[O:12]1[CH2:17][CH:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.C1(C)C=CC=CC=1>[O:12]1[CH2:13][CH:14]=[C:15]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:16][CH2:17]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 113567033,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate

Produkt 1

HCID 666330234-(3,6-dihydro-2H-pyran-4-yl)benzonitrileAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 887MethanolLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2.2 g (15.1 mmol) of (4-cyanophenyl)boronic acid, 2.5 g (10.8 mmol) of 3,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate, 373 mg (0.32 mmol) of tetrakis(triphenylphosphine)palladium(0) and 1.59 g (15.1 mmol) of sodium carbonate were heated under reflux in a mixed solvent comprising 4 mL of H2O, 57 mL of toluene, and 17 mL of methanol for 3 hours. After the completion of the reaction, the organic solvent was distilled off under reduced pressure, H2O was added to the residue, and ethyl acetate extraction was performed. Subsequently, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 1.27 g of 4-(3,6-dihydro-2H-pyran-4-yl)benzonitrile (yield: 64%).

Aufarbeitung

  1. customAfter the completion of the reaction
  2. distillationthe organic solvent was distilled off under reduced pressure, H2O
  3. additionwas added to the residue, and ethyl acetate extraction
  4. dry with materialSubsequently, the organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained crude product
  7. customwas separated
  8. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-84dc698ec0df48dc914f0e16d896c0d7
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08785473B2

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