Pyridine → (1,1-Dioxo-1lambda6-thiolan-3-yl)methyl 4-methylbenzene-1-sulfonate

HRID 237420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237420
[O:1]=[S:2]1(=[O:9])[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl.Cl>[O:1]=[S:2]1(=[O:9])[CH2:6][CH2:5][CH:4]([CH2:7][O:8][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH2:3]1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 36944633-(Hydroxymethyl)-1lambda6-thiolane-1,1-dione

Produkt 1

HCID 18801509(1,1-Dioxo-1lambda6-thiolan-3-yl)methyl 4-methylbenzene-1-sulfonateAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of (1,1-dioxo-tetrahydro-1lambda*6*-thiophen-3-yl)-methanol (3.59 g), 4-toluenesulfonyl chloride (9.11 g) and pyridine 5.8 mL) in chloroform (50 mL) was heated to 60° C. and stirred overnight. The reaction mixture was cooled and diluted with 100 mL 1N HCl and extracted with methylene chloride. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (60% EtOAc in hexanes) to give 4.012 g of toluene-4-sulfonic acid 1,1-dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethyl ester.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with methylene chloride
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d14bb462408d442b9f2b7c1625a65077
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642601B2

Notizen zur Reaktion

Wird geladen…