Pyridine → 3-Butynyl p-toluenesulfonate

HRID 254655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254655
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].N1C=CC=CC=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(Cl)Cl>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:5][CH2:1][CH2:2][C:3]#[CH:4])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 135663-Butyn-1-OL

Produkt 1

HCID 2720203-Butynyl p-toluenesulfonateAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 3-butyn-1-ol (0.5 g, 8.3 mmol) in CH2Cl2 (20 mL) and pyridine (1.7 mL, 33.2 mmol) was added p-toluenesulfonyl chloride (1.7 g, 8.7 mmol). This mixture was stirred at ambient temperature for 16 h then diluted with CH2Cl2 (20 mL) and quenched with aqueous 1% HCl (5 mL). The layers were separated and the organic layer was washed with aqueous 1% HCl (5 mL) and brine (5 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (4:1 hexanes:EtOAc) to provide the title compound (0.30 g, 1.3 mmol, 16% yield). MS (DCI/NH3) m/z 242 (M+NH4)+.

Aufarbeitung

  1. customquenched with aqueous 1% HCl (5 mL)
  2. customThe layers were separated
  3. washthe organic layer was washed with aqueous 1% HCl (5 mL) and brine (5 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified via column chromatography (4:1 hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e3c3a39e5ca64d50be83651cd5226594
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875640B2

Notizen zur Reaktion

Wird geladen…