4-Toluenesulfonyl chloride → Iodopropargyl 4methylbenzenesulfonate

HRID 258241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 258241
[I:1][CH:2]([OH:5])[C:3]#[CH:4].[OH-].[Na+].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C1COCC1.O>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:5][CH:2]([I:1])[C:3]#[CH:4])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 602749Iodopropargyl alcohol

Produkt 1

HCID 18321752Iodopropargyl 4methylbenzenesulfonateAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Into a 500 mL 4-neck round bottom flask, equipped with a magnetic stirrer and an addition funnel, in an ice bath were placed iodopropargyl alcohol (10 g, 54.9 mmol) in THF (20 mL) and sodium hydroxide (3.4 g, 84.6 mmol) in water (20 mL) To the above cold mixture was added a solution of p-toluenesulfonyl chloride (10.4 g, 54.95 mmol) in THF (20 mL) from an addition funnel. The reaction mixture was stirred for 2 hrs. below 5° C. The reaction mixture was then poured into ice water and the precipitate was collected by suction-filtration and washed with water. After drying under vacuum, the precipitate afforded 17.2 g (yield: 93.4%) of iodopropargyl 4-methylbenzenesulfonate as an off-white solid, mp=75°-78° C. An NMR spectrum showed the desired compound.

Aufarbeitung

  1. customInto a 500 mL 4-neck round bottom flask, equipped with a magnetic stirrer and an addition funnel, in an ice bath
  2. custombelow 5° C
  3. filtrationthe precipitate was collected by suction-filtration
  4. washwashed with water
  5. customAfter drying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-46753b27d9034d9db66249b95f4476f7
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05266567

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