Water → 2-(4-Ethynylphenyl)pyridine

HRID 1522714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522714
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>O1CCCC1>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1)#[CH:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 692372572-[4-[2-(Trimethylsilyl)ethynyl]phenyl]pyridine

Produkt 1

HCID 860848412-(4-Ethynylphenyl)pyridineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (2) (2.26 g, 8.97 mmol) and tetrabutylammonium fluoride (1 M in tetrahydrofuran, 36 mL, 36 mmol) in tetrahydrofuran was stirred at room temperature under argon for 3 hours. Dichloromethane (100 mL) and water (150 mL) were added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×15 mL). The combined organic layers were washed with brine (200 mL), dried over anhydrous magnesium sulfate, filtered and the solvent completely removed. The residue was purified by passing through a silica plug using dichloromethane as eluent to give (3) (1.44 g, 90%).

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (3×15 mL)
  3. washThe combined organic layers were washed with brine (200 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent completely removed
  7. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-36fe1fb911cf4719bd5f1ea438ae9d0d
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09078330B2

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