4-Toluenesulfonyl chloride → HCID 53748711, Verbindung

HRID 597696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597696
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:21])[CH2:13][CH2:14][CH:15]=[CH:16][C:17]#[C:18][CH2:19][CH3:20]>N1C=CC=CC=1>[S:7]([O:21][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][C:17]#[C:18][CH2:19][CH3:20])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 71373320Non-4-en-6-yn-1-ol

Produkt 1

HCID 53748711HCID 53748711, VerbindungAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixture of p-toluenesulfonyl chloride (22.4 g., 0.12 moles) and 50 ml. of anhydrous pyridine is added 14 g. of non-4-en-6-yn-1-ol (0.107 moles) with ice bath cooling. The mixture is stirred for 1 hour and then is stored at 0° overnight. Ice is added to the mixture which is extracted with several portions of 50:50 ether/hexane. The combined organic phase is washed with 5% HCl, water, saturated sodium bicarbonate and dried over sodium sulfate. Removal of solvent at reduced pressure and subsequent solvent removal at 0.15 mm. for one hour gives 1-tosyloxy-non-4-en-6-yne (28 g.).

Aufarbeitung

  1. waitis stored at 0° overnight
  2. additionIce is added to the mixture which
  3. extractionis extracted with several portions of 50:50 ether/hexane
  4. washThe combined organic phase is washed with 5% HCl, water, saturated sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. customRemoval of solvent
  7. customat reduced pressure and subsequent solvent removal at 0.15 mm

Quellen und Nachweise

ORD-Eintrag
ord-a016e56238114751882e7381b63fc91d
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04014946

Notizen zur Reaktion

Wird geladen…