Pyridine → (5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 481719

Reaktionsgleichung

Reaktionsgleichung von HRID 481719
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][CH:14]1[O:18][C:17](=[O:19])[CH2:16][CH2:15]1.N1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH:14]2[O:18][C:17](=[O:19])[CH2:16][CH2:15]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 984315-(Hydroxymethyl)oxolan-2-one

Produkt 1

HCID 4609541(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

p-Toluenesulfonyl chloride (23.65 g, 124.03 mmol) was added portion wise to a solution of (±)-dihydro-5-hydroxymethyl-2(3H)-furanone (example 56) (11.07 g, 95.43 mmol) and pyridine (15.4 mL, 190.86 mmol) in methylene chloride (300 mL) at 0° C. The solution was allowed to warm to rt and stirred overnight. The solution was then washed with water (2×100 mL), 0.5 n HCl until the washings were acidic and finally with saturated NaHCO3. After drying and concentrating, the residue was triturated with toluene to give the title compound as a white solid (19.63 g, 76%).

Aufarbeitung

  1. washThe solution was then washed with water (2×100 mL), 0.5 n HCl until the washings
  2. customAfter drying
  3. concentrationconcentrating
  4. customthe residue was triturated with toluene

Quellen und Nachweise

ORD-Eintrag
ord-9ecf2e7675374cd88f97532e780df932
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789394

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